5 methoxytryptamine trip

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5-Methoxy-N,N-diisopropyltryptamine (Foxy), a selective and high affinity inhibitor of serotonin transporter

Affiliation.

• 1 Department of Dental Pharmacology, Okayama University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Shikata 2-5-1, Okayama 700-8525, Japan.
• PMID: 17382495
• DOI: 10.1016/j.toxlet.2007.02.007

5-Methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) is a synthetic orally active hallucinogenic tryptamine derivative, known also as Foxy or Foxy methoxy. However, few studies have examined its effects in vitro. In the present study, we investigated the actions of 5-MeO-DIPT against monoamine neurotransmitter transporters, including the transporters for dopamine (DAT), norepinephrine (NET), and serotonin (SERT), using COS-7 cells heterologously expressing these transporters and rat brain synaptosomes. 5-MeO-DIPT specifically inhibited the uptake of [3H]serotonin (5-HT) by the SERT-expressing COS-7 cells and rat striatal synaptosomes in a high affinity manner at concentrations similar to those for cocaine. The effect was reversible and competitive. 5-MeO-DIPT failed to stimulate reverse transport of [3H]5-HT through SERT, while it prevented the releasing action of methamphetamine. 5-MeO-DIPT induced cell toxicity at high concentrations in COS-7 cells, and it was not influenced by the expression of SERT. These results demonstrated that 5-MeO-DIPT acts as a competitive SERT inhibitor and has an inability to cause reverse transport, underlying its serotonergic actions.

Publication types

• Research Support, Non-U.S. Gov't
• 5-Methoxytryptamine / analogs & derivatives*
• 5-Methoxytryptamine / pharmacology
• Biogenic Monoamines / antagonists & inhibitors
• Cell Survival / drug effects
• Chlorocebus aethiops
• Cocaine / pharmacology
• Methamphetamine / pharmacology
• Rats, Sprague-Dawley
• Selective Serotonin Reuptake Inhibitors / pharmacology*
• Serotonin Plasma Membrane Transport Proteins / metabolism*
• Synaptosomes / drug effects*
• Synaptosomes / metabolism
• Biogenic Monoamines
• Serotonin Plasma Membrane Transport Proteins
• Serotonin Uptake Inhibitors
• 5-methoxy-N,N-diisopropyltryptamine
• 5-Methoxytryptamine
• Methamphetamine

• Help & Feedback
• About epocrates

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• N-acétyl-5-méthoxytryptamine

Entire Monograph

Reported uses, reported doses, drug interactions, adverse reactions.

• Add to Interaction Check
• NOTE: see Herb & Supplement Effectiveness Rating Definitions table
• acute kidney injury [Insufficient Evidence]
• ADHD [Insufficient Evidence]
• age-related macular degeneration [Insufficient Evidence]
• athletic performance [Possibly Ineffective]
• atopic dermatitis (eczema) [Insufficient Evidence]
• autism spectrum disorder [Insufficient Evidence]
• benzodiazepine withdrawal [Likely Ineffective]
• bipolar disorder [Insufficient Evidence]
• BPH [Insufficient Evidence]
• bronchopulmonary dysplasia [Insufficient Evidence]
• CABG [Insufficient Evidence]
• cachexia [Possibly Ineffective]
• cancer, adjunct tx [Possibly Effective]
• cancer-related fatigue [Possibly Ineffective]
• cancer-related pain [Possibly Ineffective]
• chronic fatigue syndrome [Insufficient Evidence]
• cluster headache [Insufficient Evidence]
• cognitive impairment [Insufficient Evidence]
• colorectal CA [Insufficient Evidence]
• contraception [Insufficient Evidence]
• COPD [Insufficient Evidence]
• COVID-19 [Insufficient Evidence]
• critical illness (trauma) [Possibly Ineffective]
• delayed sleep phase syndrome [Likely Effective]
• delirium [Insufficient Evidence]
• dementia [Possibly Ineffective]
• depression [Likely Ineffective]
• diabetes mellitus [Insufficient Evidence]
• diabetic neuropathy [Insufficient Evidence]
• dysmenorrhea [Insufficient Evidence]
• dyspepsia [Insufficient Evidence]
• emergence delirium [Possibly Effective]
• endometriosis [Insufficient Evidence]
• endotracheal intubation-related hemodynamic effects [Insufficient Evidence]
• epilepsy [Insufficient Evidence]
• fibromyalgia [Insufficient Evidence]
• GERD [Insufficient Evidence]
• H. pylori infection [Insufficient Evidence]
• heart failure [Insufficient Evidence]
• HTN [Possibly Effective]
• IBS [Insufficient Evidence]
• infertility [Possibly Ineffective]
• insomnia [Possibly Effective]
• ischemic reperfusion injury [Insufficient Evidence]
• jet lag [Possibly Effective]
• lung CA [Insufficient Evidence]
• melasma [Insufficient Evidence]
• menopausal sx [Insufficient Evidence]
• metabolic syndrome [Insufficient Evidence]
• MI [Insufficient Evidence]
• migraine prophylaxis [Possibly Effective]
• multiple sclerosis [Insufficient Evidence]
• neonatal encephalopathy [Insufficient Evidence]
• nocturnal enuresis [Insufficient Evidence]
• nonalcoholic fatty liver dz [Insufficient Evidence]
• non-24h sleep-wake disorder, blind pts [Likely Effective]
• obesity [Insufficient Evidence]
• oral mucositis, chemo-or XRT-related [Insufficient Evidence]
• osteopenia [Insufficient Evidence]
• osteoporosis [Insufficient Evidence]
• pain, acute [Insufficient Evidence]
• pain, chronic [Insufficient Evidence]
• periodontitis [Insufficient Evidence]
• polycystic ovary syndrome [Insufficient Evidence]
• postop nausea/vomiting [Insufficient Evidence]
• postop pain [Insufficient Evidence]
• postop recovery [Insufficient Evidence]
• postop sleep disturbance [Insufficient Evidence]
• postural tachycardia syndrome [Insufficient Evidence]
• pre-eclampsia [Insufficient Evidence]
• preop anxiety [Possibly Effective]
• preop sedation [Possibly Effective]
• prostate CA [Insufficient Evidence]
• pruritus [Insufficient Evidence]
• radiation dermatitis [Insufficient Evidence]
• REM sleep behavior disorder [Insufficient Evidence]
• renal failure [Insufficient Evidence]
• renal transplant [Insufficient Evidence]
• restless legs syndrome [Insufficient Evidence]
• rheumatoid arthritis [Insufficient Evidence]
• sarcoidosis [Insufficient Evidence]
• schizophrenia [Insufficient Evidence]
• seasonal affective disorder [Insufficient Evidence]
• sepsis [Insufficient Evidence]
• shift-work disorder [Possibly Ineffective]
• smoking cessation [Insufficient Evidence]
• stabbing headache [Insufficient Evidence]
• stress [Insufficient Evidence]
• sunburn [Possibly Effective]
• tardive dyskinesia [Insufficient Evidence]
• temporomandibular disorder [Possibly Effective]
• tension headache [Insufficient Evidence]
• thrombocytopenia, chemo-related [Possibly Effective]
• tinnitus [Insufficient Evidence]
• traumatic brain injury [Insufficient Evidence]
• ulcerative colitis [Insufficient Evidence]
• xerostomia [Insufficient Evidence]

Safety/efficacy may not be established; reported doses may be derived from limited or potentially inadequate studies w/ variable regimens, multi-ingredient products, or where concentration of active ingredients may vary widely

Special Note, COVID-19

Effectiveness ratings, acute kidney injury, adhd, peds pts, age-related macular degeneration, atopic dermatitis, peds pts, autism spectrum disorder, peds pts, bipolar disorder, bronchopulmonary dysplasia, peds pts, cancer, adjunct tx, chronic fatigue syndrome, cluster headache, cognitive impairment, delayed sleep phase syndrome, adult pts, delayed sleep phase syndrome, peds pts.

• diabetes mellitus

diabetic neuropathy

Dysmenorrhea, emergence delirium, adult pts, emergence delirium, peds pts, endometriosis, endotracheal intubation-related hemodynamic effects, epilepsy, adult pts, epilepsy, peds pts, fibromyalgia, h. pylori infection, heart failure, insomnia, adult pts, insomnia, peds pts, ischemic reperfusion injury, menopausal sx, metabolic syndrome, migraine prophylaxis, adult pts, migraine prophylaxis, peds pts, neonatal encephalopathy, nonalcoholic fatty liver dz, non-24h sleep-wake disorder, adult pts, non-24h sleep-wake disorder, peds pts, oral mucositis, chemo-or xrt-related, pain, acute, pain, chronic, periodontitis, polycystic ovary syndrome, postop pain, postop recovery, postural tachycardia syndrome, pre-eclampsia, preop anxiety, adult pts, preop anxiety, peds pts, preop sedation, adult pts, preop sedation, peds pts, prostate ca, radiation dermatitis, rem sleep behavior disorder, renal failure, sarcoidosis, schizophrenia, seasonal affective disorder, sepsis, adult pts, sepsis, peds pts, smoking cessation, tardive dyskinesia, temporomandibular disorder, tension headache, thrombocytopenia, chemo-related, ulcerative colitis.

• bleeding disorders
• breastfeeding
• pregnancy or planned pregnancy
• organ transplant recipients
• seizure disorder

herb/supplement

• CYP1A2 substrate
• CNS depression

Avoid/Use Alternative

• betamethasone

melatonin + betamethasone

avoid combo : combo may interfere w/ immunosuppressive therapy (antagonistic effects)

melatonin + butalbital

avoid combo : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

melatonin + codeine

avoid combo if antitussive use; otherwise monitor resp. rate; decr. dose of one or both drugs, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

melatonin + cortisone

melatonin + doxylamine

avoid combo if doxylamine use for pregnancy-related nausea/vomiting, otherwise caution advised : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

melatonin + ethanol

• hydrocodone

melatonin + hydrocodone

• hydrocortisone

melatonin + hydrocortisone

• isocarboxazid

melatonin + isocarboxazid

use alternative during and x10 days after isocarboxazid use : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

melatonin + kava

avoid combo : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

melatonin + kratom

use alternative or monitor resp. rate : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

melatonin + metaxalone

use alternative or monitor resp. rate : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

• methylprednisolone

melatonin + methylprednisolone

• metoclopramide

melatonin + metoclopramide

use alternative : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

melatonin + midazolam

use alternative or monitor resp. rate; use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

melatonin + oxybate

use alternative or monitor resp. rate; decr. dose of one or both drugs : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment, hypotension, syncope (additive effects)

melatonin + phenelzine

• prednisolone

melatonin + prednisolone

• promethazine

melatonin + promethazine

use alternative or monitor resp. rate; decr. dose of one or both drugs : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

• ropeginterferon alfa-2b

melatonin + ropeginterferon alfa-2b

• thalidomide

melatonin + thalidomide

use alternative or consider decr. dose of one or both drugs : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

• tranylcypromine

melatonin + tranylcypromine

• trimethobenzamide

melatonin + trimethobenzamide

use alternative or consider decr. dose of one or both drugs : combo may incr. risk of sedation, other adverse effects (additive effects)

melatonin + zuranolone

Monitor/Modify Tx

• aldesleukin

melatonin + aldesleukin

withhold aldesleukin if mod-severe somnolence occurs; otherwise, caution advised : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

melatonin + alfentanil

monitor BP, resp. rate; decr. dose of one or both drugs : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment, hypotension (additive effects)

melatonin + alprazolam

monitor resp. rate : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

• buprenorphine

melatonin + buprenorphine

monitor resp. rate; decr. dose of one or both drugs, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• butorphanol

melatonin + butorphanol

monitor resp. rate, decr. dose of one or both drugs, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• chlorpromazine

melatonin + chlorpromazine

consider decr. dose of one or both drugs : combo may incr. risk of sedation, other adverse effects (additive effects)

melatonin + clonazepam

• daridorexant

melatonin + daridorexant

consider decr. dose of one or both drugs : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

melatonin + desflurane

consider decr. dose of one or both drugs : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

• dexmedetomidine

melatonin + dexmedetomidine

• dexmedetomidine injection

melatonin + dexmedetomidine injection

monitor resp. rate, consider decr. dose of one or both drugs : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

melatonin + diazepam

monitor resp. rate, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• dihydrocodeine

melatonin + dihydrocodeine

melatonin + droperidol

decr. dose of one or both drugs : combo may incr. risk of sedation, other adverse effects (additive effects)

melatonin + esketamine

• eszopiclone

melatonin + eszopiclone

melatonin + fentanyl

• fluphenazine

melatonin + fluphenazine

melatonin + gabapentin

monitor resp. rate : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• gabapentin enacarbil

melatonin + gabapentin enacarbil

• hydromorphone

melatonin + hydromorphone

• hydroxyzine

melatonin + hydroxyzine

melatonin + ifosfamide

D/C one or both drugs if encephalopathy occurs : combo may incr. risk of sedation, other adverse effects (additive effects)

melatonin + ketamine

monitor resp. rate; use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• levorphanol

melatonin + levorphanol

melatonin + lorazepam

melatonin + meperidine

melatonin + methadone

• mirtazapine

melatonin + mirtazapine

melatonin + morphine

melatonin + nalbuphine

melatonin + nelarabine

withhold nelarabine if Grade 2 or greater somnolence occurs : combo may incr. risk of sedation, other adverse effects (additive effects)

melatonin + nifedipine

monitor BP : combo may decr. antihypertensive efficacy of nifedipine (mechanism unknown)

melatonin + olanzapine

monitor BP : combo may incr. risk of CNS depression, psychomotor impairment, hypotension, incl. orthostasis (additive effects)

• oliceridine

melatonin + oliceridine

monitor resp. rate, BP; decr. dose of one or both drugs, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment, hypotension (additive effects)

melatonin + opicapone

melatonin + opium

melatonin + oxybutynin

decr. dose of one or both drugs or consider oxybutynin transdermal patch : combo may incr. risk of CNS depression, psychomotor impairment; somnolence less likely w/ oxybutynin transdermal patch (additive effects)

melatonin + oxycodone

monitor resp. rate; consider decr. dose of one or both drugs, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• oxymorphone

melatonin + oxymorphone

monitor resp. rate, consider decr. dose of one or both drugs, use lowest effective doses and shortest duration of concomitant tx : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

• pentazocine

melatonin + pentazocine

• pentobarbital

melatonin + pentobarbital

• perphenazine

melatonin + perphenazine

• phenobarbital

melatonin + phenobarbital

melatonin + pregabalin

melatonin + primidone

melatonin + propofol

• remifentanil

melatonin + remifentanil

• remimazolam

melatonin + remimazolam

• sevoflurane

melatonin + sevoflurane

melatonin + sufentanil

monitor resp. rate, decr. sufentanil start dose, consider decr. melatonin dose, use lowest effective doses : combo may incr. risk of profound CNS and resp. depression, psychomotor impairment (additive effects)

melatonin + suvorexant

melatonin + tapentadol

• thioridazine

melatonin + thioridazine

• thiothixene

melatonin + thiothixene

melatonin + tramadol

melatonin + warfarin

monitor INR, bleeding s/sx : combo may incr. risk of bleeding, incl. life-threatening (mechanism unknown)

melatonin + zaleplon

melatonin + ziconotide

consider decr. dose of one or both drugs : combo may incr. risk of confusion, dizziness, other CNS adverse effects (additive effects)

melatonin + zolpidem

Therapeutic Advantage

melatonin + isoniazid

use for therapeutic advantage : combo may enhance isoniazid efficacy against some Mycobacterium species (synergistic antimicrobial effects)

Caution Advised

melatonin + 5-HTP

caution advised : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

• allopurinol

melatonin + allopurinol

• almotriptan

melatonin + almotriptan

melatonin + amantadine

• amitriptyline

melatonin + amitriptyline

melatonin + amoxapine

• anti-thymocyte globulin

melatonin + anti-thymocyte globulin

caution advised : combo may interfere w/ immunosuppressive therapy (antagonistic effects)

• apomorphine

melatonin + apomorphine

• apraclonidine ophthalmic

melatonin + apraclonidine ophthalmic

caution advised if apraclonidine IOP adjunct use; postop use OK : combo may incr. risk of CNS depression, psychomotor impairment (additive effects)

• aripiprazole

melatonin + aripiprazole

• aripiprazole bimonthly injection

melatonin + aripiprazole bimonthly injection

• aripiprazole lauroxil

melatonin + aripiprazole lauroxil

melatonin + asenapine

• azathioprine

melatonin + azathioprine

melatonin + baclofen

• baclofen intrathecal

melatonin + baclofen intrathecal

caution advised : combo may incr. risk of CNS and resp. depression, psychomotor impairment (additive effects)

• basiliximab

melatonin + basiliximab

melatonin + belatacept

melatonin + belimumab

• brexanolone

melatonin + brexanolone

caution advised : combo may incr. risk of sedation, other adverse effects (additive effects)

• brexpiprazole

melatonin + brexpiprazole

• brimonidine ophthalmic

melatonin + brimonidine ophthalmic

caution advised if elevated IOP use; OTC ocular redness use OK : combo may incr. risk of sedation, other adverse effects (additive effects)

• brimonidine topical

melatonin + brimonidine topical

• brivaracetam

melatonin + brivaracetam

• bromocriptine

melatonin + bromocriptine

• brompheniramine

melatonin + brompheniramine

melatonin + buspirone

melatonin + caffeine

caution advised : combo may incr. melatonin levels, risk of adverse effects (hepatic metab. inhibited)

• caffeine citrate

melatonin + caffeine citrate

• cannabidiol

melatonin + cannabidiol

melatonin + cannabis

melatonin + capmatinib

• carbamazepine

melatonin + carbamazepine

• carbinoxamine

melatonin + carbinoxamine

• cariprazine

melatonin + cariprazine

• carisoprodol

melatonin + carisoprodol

melatonin + cenobamate

melatonin + cetirizine

• chamomile, German

melatonin + chamomile, German

• chlordiazepoxide

melatonin + chlordiazepoxide

• chlorpheniramine

melatonin + chlorpheniramine

• chlorzoxazone

melatonin + chlorzoxazone

• ciprofloxacin

melatonin + ciprofloxacin

caution advised : combo may incr. melatonin levels, risk of sedation, other adverse effects (hepatic metab. inhibited)

melatonin + citalopram

melatonin + clemastine

melatonin + clobazam

• clomipramine

melatonin + clomipramine

melatonin + clonidine

• clorazepate

melatonin + clorazepate

melatonin + clozapine

• cyclobenzaprine

melatonin + cyclobenzaprine

• cyclosporine

melatonin + cyclosporine

• cyproheptadine

melatonin + cyproheptadine

melatonin + dantrolene

• darifenacin

melatonin + darifenacin

• desipramine

melatonin + desipramine

• desvenlafaxine

melatonin + desvenlafaxine

• deutetrabenazine

melatonin + deutetrabenazine

• dexchlorpheniramine

melatonin + dexchlorpheniramine

• dichlorphenamide

melatonin + dichlorphenamide

caution advised : combo may incr. risk of sedation, adverse effects (additive effects)

• difelikefalin

melatonin + difelikefalin

melatonin + difenoxin

• dimenhydrinate

melatonin + dimenhydrinate

• diphenhydramine

melatonin + diphenhydramine

• diphenoxylate

melatonin + diphenoxylate

• domperidone

melatonin + domperidone

melatonin + doxepin

• doxepin topical

melatonin + doxepin topical

melatonin + dronabinol

melatonin + duloxetine

melatonin + efavirenz

melatonin + eletriptan

melatonin + enasidenib

melatonin + entacapone

• entrectinib

melatonin + entrectinib

• escitalopram

melatonin + escitalopram

• eslicarbazepine acetate

melatonin + eslicarbazepine acetate

melatonin + estazolam

• estradiol (contraceptive)

melatonin + estradiol (contraceptive)

• estradiol (hormone replacement)

melatonin + estradiol (hormone replacement)

• estrogens, conjugated (hormone replacement)

melatonin + estrogens, conjugated (hormone replacement)

• estrogens, esterified (hormone replacement)

melatonin + estrogens, esterified (hormone replacement)

• ethanol (in some formulations)

melatonin + ethanol (in some formulations)

• ethinyl estradiol (contraceptive)

melatonin + ethinyl estradiol (contraceptive)

• ethinyl estradiol (hormone replacement)

melatonin + ethinyl estradiol (hormone replacement)

• ethosuximide

melatonin + ethosuximide

melatonin + etomidate

melatonin + everolimus

melatonin + felbamate

• fenfluramine

melatonin + fenfluramine

• fesoterodine

melatonin + fesoterodine

• fexinidazole

melatonin + fexinidazole

• flibanserin

melatonin + flibanserin

melatonin + fluoxetine

• fluvoxamine

melatonin + fluvoxamine

caution advised, may be used for therapeutic advantage : combo may incr. melatonin levels, risk of CNS depression, psychomotor impairment, other adverse effects; combo may be useful for refractory insomnia (hepatic metab. inhibited, additive effects)

• fosphenytoin

melatonin + fosphenytoin

caution advised : combo may decr. melatonin levels, efficacy; may incr. risk of sedation, other adverse effects (hepatic metab. induced; additive effects)

• frovatriptan

melatonin + frovatriptan

melatonin + ganaxolone

melatonin + givosiran

caution advised : combo may incr. melatonin levels, risk of adverse effects (hepatic metab. inhibited; givosiran effects on hepatic heme biosynthesis may reduce CYP450 enzyme activity)

melatonin + glofitamab

• glycopyrrolate

melatonin + glycopyrrolate

melatonin + guanfacine

• haloperidol

melatonin + haloperidol

• hydroxyurea

melatonin + hydroxyurea

• hyoscyamine

melatonin + hyoscyamine

• iloperidone

melatonin + iloperidone

melatonin + imipramine

melatonin + isoflurane

melatonin + lacosamide

• lamotrigine

melatonin + lamotrigine

melatonin + lasmiditan

• leflunomide

melatonin + leflunomide

caution advised : combo may decr. melatonin levels, efficacy (hepatic metab. induced)

• lemborexant

melatonin + lemborexant

• levetiracetam

melatonin + levetiracetam

• levocetirizine

melatonin + levocetirizine

melatonin + levodopa

• levomilnacipran

melatonin + levomilnacipran

melatonin + lofexidine

melatonin + loxapine

• lumateperone

melatonin + lumateperone

melatonin + lurasidone

• lymphocyte immune globulin, anti-thymocyte globulin

melatonin + lymphocyte immune globulin, anti-thymocyte globulin

melatonin + meclizine

• meprobamate

melatonin + meprobamate

• methocarbamol

melatonin + methocarbamol

• methohexital

melatonin + methohexital

• methoxsalen

melatonin + methoxsalen

• methsuximide

melatonin + methsuximide

melatonin + methyldopa

melatonin + metyrapone

melatonin + metyrosine

melatonin + mexiletine

• milnacipran

melatonin + milnacipran

melatonin + mitotane

melatonin + molindone

• mosunetuzumab

melatonin + mosunetuzumab

• mycophenolate mofetil

melatonin + mycophenolate mofetil

caution advised : combo may incr. risk of CNS depression, psychomotor impairment; may interfere w/ immunosuppressive therapy (additive effects; antagonistic effects)

• mycophenolic acid

melatonin + mycophenolic acid

melatonin + naltrexone

• naratriptan

melatonin + naratriptan

melatonin + nefazodone

• nortriptyline

melatonin + nortriptyline

• orphenadrine

melatonin + orphenadrine

• osilodrostat

melatonin + osilodrostat

melatonin + oxazepam

• oxcarbazepine

melatonin + oxcarbazepine

• paliperidone

melatonin + paliperidone

melatonin + paroxetine

• passion flower

melatonin + passion flower

melatonin + perampanel

• pheniramine

melatonin + pheniramine

melatonin + phenytoin

caution advised : combo may decr. melatonin levels, efficacy; may incr. risk of CNS depression, psychomotor impairment (hepatic metab. induced; additive effects)

melatonin + pimozide

• pramipexole

melatonin + pramipexole

• procarbazine

melatonin + procarbazine

• prochlorperazine

melatonin + prochlorperazine

• protriptyline

melatonin + protriptyline

melatonin + pyrilamine

melatonin + quazepam

melatonin + quetiapine

melatonin + ramelteon

melatonin + rasagiline

• repotrectinib

melatonin + repotrectinib

melatonin + rifampin

• risperidone

melatonin + risperidone

melatonin + ritonavir

• rizatriptan

melatonin + rizatriptan

melatonin + ropinirole

• rotigotine transdermal

melatonin + rotigotine transdermal

caution advised : combo may incr. risk of sedation, psychomotor impairment (additive effects)

melatonin + rucaparib

melatonin + rufinamide

melatonin + safinamide

• scopolamine

melatonin + scopolamine

melatonin + selegiline

• selegiline transdermal

melatonin + selegiline transdermal

melatonin + selinexor

melatonin + sertraline

melatonin + sirolimus

• solifenacin

melatonin + solifenacin

• St. John's wort

melatonin + St. John's wort

• stiripentol

melatonin + stiripentol

• sumatriptan

melatonin + sumatriptan

melatonin + tacrolimus

• tasimelteon

melatonin + tasimelteon

melatonin + temazepam

• temsirolimus

melatonin + temsirolimus

• teriflunomide

melatonin + teriflunomide

• tetrabenazine

melatonin + tetrabenazine

melatonin + tiagabine

melatonin + tizanidine

melatonin + tolcapone

• tolterodine

melatonin + tolterodine

melatonin + topiramate

melatonin + trazodone

melatonin + triazolam

• trifluoperazine

melatonin + trifluoperazine

• trihexyphenidyl

melatonin + trihexyphenidyl

• trimipramine

melatonin + trimipramine

• triprolidine

melatonin + triprolidine

melatonin + trospium

• valbenazine

melatonin + valbenazine

melatonin + valerian

• valproic acid

melatonin + valproic acid

• vemurafenib

melatonin + vemurafenib

• venlafaxine

melatonin + venlafaxine

melatonin + vigabatrin

melatonin + vilazodone

melatonin + viloxazine

caution advised : combo may incr. melatonin levels, risk of CNS depression, psychomotor impairment, other adverse effects (hepatic metab. inhibited, additive effects)

• ziprasidone

melatonin + ziprasidone

• zolmitriptan

melatonin + zolmitriptan

melatonin + zonisamide

• abdominal cramps
• abdominal pain
• abnormal feces
• aggressiveness
• alertness decr.
• appetite decr.
• autoimmune hepatitis
• behavioral changes
• circadian rhythm disruption
• constipation
• cutaneous flushing
• depression, transient
• disorientation
• enuresis incr.
• esophagitis
• gynecomastia (long-term use)
• fixed drug eruption
• hallucinations
• hyponatremia
• hypotension
• IOP incr. (high-dose use)
• irritability
• menstrual flow changes
• mood changes
• muscle weakness
• nervousness
• nocturnal awakening
• sperm conc. decr.
• sperm motility decr.
• taste disturbance
• 5-methoxy-N-acetyltryptamine
• N-acetyl-5-methoxytryptamine
• pineal hormone
• Pregnancy:   possibly unsafe; avoid use
• Lactation:   insufficient data available; avoid use
• Pediatric pts:   possibly safe when used orally, low dose, short-term

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N-Acetyl-5-methoxytryptamine (also known as melatonin [2] ) is a hormone of the tryptamine class. It is found in animals, plants, fungi, and bacteria. In animals, it functions as a hormone that anticipates the daily onset of darkness; [3] it may have different functions in other organisms.

Melatonin is active and can be taken sublingually and buccaly by placing it into one's mouth and allowing it to absorb over a period of 15-25 minutes. It is less active when taken orally .

Melatonin is commonly used as a medication for insomnia; however, there is insufficient scientific evidence to prove any benefit in this area. [4] It is sold over-the-counter in most pharmacies within the United States and Canada. In other countries, it may require a prescription or not be available.

It should be noted that when purchasing melatonin, dosages may range from 3 - 10mg. While not dangerous, this dosage range is well beyond the effective dose of .25 mg, and may increase instances of drowsiness the next day. [5]

• 1 Chemistry
• 2 Pharmacology
• 3.1 Physical effects
• 3.2 Cognitive effects
• 3.3 After effects
• 3.4 Experience reports
• 4.1 Lethal dosage
• 4.2 Dependence and abuse potential
• 5 Legal status
• 7 External links
• 8 References

Melatonin is comprised of a monoamine chain attached to an indole ring at the third carbon. A monoamine chain is made up of an amine group attached to an ethane chain. This monoamine chain can be found in many neurotransmitters, including histamine , dopamine , adrenaline , and noradrenaline . It is also found in many psychoactive substances such as members of the tryptamine and phenethylamine chemical classes.

Melatonin, being a tryptamine, shares many structural properties with psychedelic substances. However, it lacks their associated psychedelic effects. [6] Where many tryptamines have a group bonded to the ethylamine, melatonin has an acetyl group.

Melatonin can reacted when used with Erlich reagent turning pink/red to purple (Tested with Natrol Melatonin Tablet).

Pharmacology

Melatonin is a full agonist of melatonin receptor 1 (picomolar binding affinity) and melatonin receptor 2 (nanomolar binding affinity), both of which belong to the class of G-protein coupled receptors (GPCRs). [7] Melatonin receptors 1 and 2 are both G i/o -coupled GPCRs, although melatonin receptor 1 is also G q -coupled. [7] Melatonin also acts as a high-capacity free radical scavenger within mitochondria which also promotes the expression of antioxidant enzymes such as superoxide dismutase, glutathione peroxidase, glutathione reductase, and catalase via signal transduction through melatonin receptors. [7] Melatonin is metabolized in the liver by cytochrome P450 enzyme CYP1A2 to 6-hydroxymelatonin. Metabolites are conjugated with sulfuric acid or glucuronic acid for excretion in the urine. 5% of melatonin is excreted in the urine as the unchanged drug. [8] Some of the metabolites formed via the reaction of melatonin with a free radical include cyclic 3-hydroxymelatonin, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK), and N1-acetyl-5-methoxykynuramine (AMK). [7]

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index ( SEI ), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors . As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

• Sedation - Melatonin does not produce sedation in the manner of central nervous depressants like alcohol , benzodiazepines , or zolpidem .
• Physical euphoria - This effect can occur alongside Muscle relaxation , and is only present at heavy dosages when the user resists the urge to sleep.
• Decreased libido - This effect can be caused by the Sedation or by the fact that melatonin can inhibit secretion of hormones that control sexual functions. [ citation needed ]

Cognitive effects

• Sleepiness - Regarding its effects on the user's physical energy levels, melatonin is commonly considered to facilitate sleepiness. It is often used and sold as a sleep aid and mimics one's natural circadian cycle.
• Anxiety Suppression or Anxiety - Although this substance decreases anxiety with most people, it can also cause anxiety by some.
• Dream potentiation - Melatonin is extremely effective at increasing the duration, occurrence, and vividness of dreams. It is very common for people to note that their dreams had noticeably increased the morning after ingesting melatonin as a sleep aid. Melatonin is sometimes used to increase the chances of lucid dreaming.
• Depersonalization - Depersonalization can present itself upon the come-up and persist well into the next day if the user has ingested a massive dose.
• Irritability Irritability is only present at high dosages when the user resists the urge to sleep.

After effects

• Headaches - A small subset of people may experience headaches the day after ingesting melatonin. [10]

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index . Additional experience reports can be found here:

• Erowid Experience Vaults: Melatonin

Toxicity and harm potential

Melatonin is non-addictive, not known to be harmful, and has an extremely low toxicity relative to dose. Similar to other tryptamines , there are relatively few physical side effects associated with acute melatonin exposure. Various studies have shown that in reasonable doses in a careful context, it presents no negative cognitive, psychiatric, or toxic physical consequences.

Melatonin appears to cause very few side effects as tested in the short-term (up to three months) at low doses. Two systematic reviews found no adverse effects of melatonin usage in several clinical trials, while comparative trials found the adverse effects headaches, dizziness, nausea, and drowsiness were reported about equally for both melatonin and placebo. [11] [12] Prolonged-release melatonin is safe with long-term use of up to 12 months. [13]

Lethal dosage

The median lethal dose of melatonin at which 50% of participants die ( LD 50 ) for human beings has never been reached in any setting.

Dependence and abuse potential

Melatonin is not habit-forming. It is possible, however, to develop a mild physical dependency if this compound is used on a nightly basis for a prolonged period. This simply means that if one suddenly stops their usage of the substance without tapering, they may have trouble sleeping for a couple of days afterward.

Tolerance to the effects of melatonin is slowly built after prolonged and repeated usage. After that, it takes about 7 days for the tolerance to be reduced to half and 14 days to be back at baseline (in the absence of further consumption). Melatonin presents cross-tolerance with no other known compounds, meaning that after the use of melatonin, other psychoactive compounds will not have a reduced effect.

Legal status

• in modified release tablets containing 2 mg or less of melatonin for monotherapy for the short term treatment of primary insomnia characterised by poor quality of sleep for adults aged 55 or over, in packs containing not more than 30 tablets. [14]
• Canada : Melatonin is freely available to purchase as a dietary supplement and can be found at most pharmacies and grocery stores across the country. [15]
• Germany : Melatonin is a prescription medicine, according to Anlage 1 AMVV. [16] It is however available as a dietary supplement in certain forms, often in low dosages or as combination preparations. [17]
• India : Melatonin is legal to purchase as a dietary supplement. [ citation needed ]
• Italy : Melatonin is legal to purchase as a dietary supplement. [ citation needed ]
• Ireland : Melatonin is a prescription-only medicine. [18]
• Sweden : Melatonin is an over-the-counter medication in small amounts, but generally a prescription pharmaceutical. [19]
• Switzerland : Melatonin is listed as a "Abgabekategorie B" pharmaceutical, which generally requires a prescription. [20]
• United Kingdom : Melatonin is a licensed prescription-only medicine (POM) in the United Kingdom. [21] It is not a criminal offense to possess this medicine without a valid prescription. This medicine can legally be obtained with a valid prescription or through legal import of the medicine for personal use as outlined in Section 13 of the Medicines Act 1968. [22]
• United States : Melatonin is listed as an uncontrolled substance and is legal to possess and distribute, and is freely available to purchase as a dietary supplement. [23]
• Responsible use
• Neurotransmitter

External links

• Melatonin (Wikipedia)
• Melatonin as a medication and supplement (Wikipedia)
• Melatonin (Erowid Vault)
• Melatonin (TiHKAL / Isomer Design)
• Melatonin (DrugBank)
• Melatonin (Drugs.com)
• Melatonin (Examine)
• ↑ DeMuro, R. L., Nafziger, A. N., Blask, D. E., Menhinick, A. M., Bertino, J. S. (July 2000). "The Absolute Bioavailability of Oral Melatonin" . The Journal of Clinical Pharmacology . 40 (7): 781–784. doi : 10.1177/00912700022009422 . ISSN   0091-2700 .  
• ↑ Sleepdex: Melatonin  
• ↑ Hardeland, R., Pandi-Perumal, S. R., Cardinali, D. P. (March 2006). "Melatonin". The International Journal of Biochemistry & Cell Biology . 38 (3): 313–316. doi : 10.1016/j.biocel.2005.08.020 . ISSN   1357-2725 .  
• ↑ Brasure, M., MacDonald, R., Fuchs, E., Olson, C. M., Carlyle, M., Diem, S., Koffel, E., Khawaja, I. S., Ouellette, J., Butler, M., Kane, R. L., Wilt, T. J. (2015). Management of Insomnia Disorder . AHRQ Comparative Effectiveness Reviews. Agency for Healthcare Research and Quality (US).  
• ↑ Mundey, K., Benloucif, S., Harsanyi, K., Dubocovich, M. L., Zee, P. C. (October 2005). "Phase-dependent treatment of delayed sleep phase syndrome with melatonin". Sleep . 28 (10): 1271–1278. doi : 10.1093/sleep/28.10.1271 . ISSN   0161-8105 .  
• ↑ Erowid Online Books : “TIHKAL” - #35 MELATONIN  
• ↑ 7.0 7.1 7.2 7.3 J Jockers, R., Delagrange, P., Dubocovich, M. L., Markus, R. P., Renault, N., Tosini, G., Cecon, E., Zlotos, D. P. (September 2016). "Update on melatonin receptors: IUPHAR Review 20". British Journal of Pharmacology . 173 (18): 2702–2725. doi : 10.1111/bph.13536 . ISSN   1476-5381 .  
• ↑ Tordjman, S., Chokron, S., Delorme, R., Charrier, A., Bellissant, E., Jaafari, N., Fougerou, C. (April 2017). "Melatonin: Pharmacology, Functions and Therapeutic Benefits". Current Neuropharmacology . 15 (3): 434–443. doi : 10.2174/1570159X14666161228122115 . ISSN   1875-6190 .  
• ↑ 9.0 9.1 Pozo, M. J., Gomez-Pinilla, P. J., Camello-Almaraz, C., Martin-Cano, F. E., Pascua, P., Rol, M. A., Acuña-Castroviejo, D., Camello, P. J. (2010). "Melatonin, a potential therapeutic agent for smooth muscle-related pathological conditions and aging". Current Medicinal Chemistry . 17 (34): 4150–4165. doi : 10.2174/092986710793348536 . ISSN   1875-533X .  
• ↑ Melatonin (Melatonin Time Release) - Side Effects, Interactions, Uses, Dosage, Warnings  
• ↑ Buscemi, N., Vandermeer, B., Hooton, N., Pandya, R., Tjosvold, L., Hartling, L., Baker, G., Klassen, T. P., Vohra, S. (December 2005). "The Efficacy and Safety of Exogenous Melatonin for Primary Sleep Disorders" . Journal of General Internal Medicine . 20 (12): 1151–1158. doi : 10.1111/j.1525-1497.2005.0243.x . ISSN   0884-8734 .  
• ↑ Buscemi, N., Vandermeer, B., Hooton, N., Pandya, R., Tjosvold, L., Hartling, L., Vohra, S., Klassen, T. P., Baker, G. (18 February 2006). "Efficacy and safety of exogenous melatonin for secondary sleep disorders and sleep disorders accompanying sleep restriction: meta-analysis" . BMJ : British Medical Journal . 332 (7538): 385–393. doi : 10.1136/bmj.38731.532766.F6 . ISSN   0959-8138 .  
• ↑ Lyseng-Williamson, K. A. (November 2012). "Melatonin prolonged release: in the treatment of insomnia in patients aged ≥55 years". Drugs & Aging . 29 (11): 911–923. doi : 10.1007/s40266-012-0018-z . ISSN   1179-1969 .  
• ↑ Health, Poisons Standard February 2022  
• ↑ https://health-products.canada.ca/lnhpd-bdpsnh/info?licence=80015830
• ↑ Anlage 1 AMVV - Einzelnorm  
• ↑ Moll, D. (2019), Melatonin in Nahrungsergänzungsmitteln  
• ↑ https://www.hpra.ie/homepage/medicines/medicines-information/find-a-medicine/results/item?pano=EU/1/07/392/001&t=Circadin
• ↑ ”Receptfritt melatonin på apoteken”. janusinfo.se .
• ↑ https://www.swissmedic.ch/swissmedic/de/home/services/listen_neu.html
• ↑ https://www.nhs.uk/medicines/melatonin/about-melatonin/
• ↑ "Medicines Act 1968 Section 13" .  
• ↑ https://www.drugs.com/melatonin.html
• Dietary supplement
• All articles with unsourced statements
• Articles with unsourced statements

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UNC Basketball: Top-Five Prep Finalizing Date for Trip to Chapel Hill

Five-star recruit Darryn Peterson plans to check out the UNC basketball program soon.

• Author: Matt Giles

In this story:

A few months ago, Huntington Prep (W.Va.) standout Darryn Peterson announced eight finalists in his recruitment, including his long-time UNC basketball suitors, along with Arkansas, Baylor, Kentucky, Indiana, Ohio State, Michigan, and Kansas. However, he recently noted plans to expand his search for a college destination, no longer limiting it to the eight schools he named.

Even so, UNC basketball head coach Hubert Davis and his staff appear to be among Peterson's favorites. After all, the 6-foot-5, 195-pound phenom, a smooth five-star who ranks No. 3 overall and No. 1 among guards on the 247Sports 2025 Composite, told Rivals' Rob Cassidy over the weekend that he's now finalizing plans to visit Chapel Hill.

And it seems Peterson, who has previously applied the "Guard University" tag when talking about UNC since receiving an offer from the Tar Heels over a year ago, is eagerly awaiting the opportunity to check out the program in person.

"I'm excited to see what it's like down there [at UNC]," Peterson explained to Cassidy. "I watched some of their games this year, and I've been waiting to take this official visit for a while. Watching RJ Davis and how ball-dominant he was and how he got to hoop this year, I feel like if I go there we could have similar games."

adidas 3SSB Omaha | Offensive MVP 💰 Darryn Peterson | Phenom United (OH) | 2025 Averages ➡️ 23.7 PPG, 7.7 RPG, 2.3 APG, 3.0 SPG All-Circuit Awards ⤵️ https://t.co/ZBDMzC9BbE @Phenom_United @PetersonDarryn @3SSBCircuit 🎥 @n8buss pic.twitter.com/wNlg489cOV — The Circuit (@TheCircuit) April 16, 2024

Darryn Peterson, one of nine five-star talents on the 2025 UNC basketball offer sheet, added that Kansas, Ohio State, Arkansas, and Kentucky are among his other most active suitors.

RELATED: Another Elite 2025 Tar Heel Target May Reopen Recruitment

Stay tuned to All Tar Heels on SI for more UNC basketball recruiting news.

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China's president arrives in Europe to reinvigorate ties at a time of global tensions

Chinese President Xi Jinping is kicking off a three-country trip to Europe with the continent divided over how to deal with Beijing’s growing power and the U.S.-China rivalry

PARIS — Chinese President Xi Jinping kicked off a three-country trip to Europe on Sunday with the continent divided over how to deal with Beijing’s growing power and the U.S.-China rivalry.

European carmakers are losing ground to subsidized Chinese electric vehicles . Diplomats fret about alleged Chinese spies in European capitals. And China’s continued defense trade with Russia worries anyone in Europe who supports war-ravaged Ukraine and fears that the Russian army won’t stop there.