α-Methyltryptamine
Clinical data
Routes of
administration
Oral , Insufflation , Rectal , Smoked , IM , IV [1]
ATC code
Legal status
Legal status
Identifiers
1-(1H -Indol-3-yl)propan-2-amine
Synonyms
Indopan; IT-290, IT-403, U-14,164E, 3-IT[1]
CAS Number
PubChem CID
DrugBank
ChemSpider
ChEBI
ChEMBL
ECHA InfoCard
100.005.522
Chemical and physical data
Formula
C 11 H 14 N 2
Molar mass
174.24 g/mol
3D model (Jmol )
InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3
Y
Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N
Y
(verify)
α-Methyltryptamine (abbreviated as αMT , AMT ) is a psychedelic , stimulant , and entactogen drug of the tryptamine class.[2] [3] It was originally developed as an antidepressant by workers at Upjohn in the 1960s,[4] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.[5] [6] [7]
Chemistry [ edit ]
αMT is tryptamine with a methyl substituent at the alpha carbon . This alpha substitution makes it a relatively poor substrate for Monoamine_oxidase_A , thereby prolonging αMT's half-life, allowing it to reach the brain and enter the central nervous system. Its chemical relation to tryptamine is analogous to that of amphetamine to phenethylamine , amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action .
Pharmacology [ edit ]
αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines ; serotonin , norepinephrine , and dopamine ,[8] and as a non-selective serotonin receptor agonist .[9]
MAOI activity [ edit ]
αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro [10] and in-vivo .[11]
In rats the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[note 1] Dexamphetamine did not enhance the 5-hydroxytryptophan -induced rise of serotonin at any level.[12]
A typical dose of harmaline for MAO inhibition is 150 mg,[13] higher than any typical αMT dose[14] so αMT's MAOI activity at typical doses will be significant but not total. The danger rises exponentially as αMT doses approach 150 mg due to increased monoamine release and increased MAO inhibition.[clarification needed ]
Metabolism [ edit ]
2-Oxo-αMT, 6-hydroxy-αMT,[15] 7-hydroxy-αMT and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats .[16]
Dosage and effects [ edit ]
With 20–30 milligrams, euphoria , empathy , and psychedelic effects become apparent and can last as long as 12 hours.[17] A dose exceeding 40 mg is generally considered as strong. In rare cases or extreme doses the duration of effects might exceed 24 hours. αMT in freebase form is reported by users to have been smoked , with doses of between and 2–5 milligrams being cited.[1] [2]
Reported side effects include anxiety , restlessness, muscle tension , jaw tightness , pupil dilation , tachycardia , headaches , nausea , and vomiting , among other effects that might commonly be attributed to LSD , psilocybin , DMT and MDMA , such as open-eye visuals, closed eye visuals and an altered state of mind.[2] [18]
In spite of some reported experiential similarities to MDMA, the chemicals are structurally unrelated; αMT is a tryptamine while MDMA is a phenethylamine .
Like many other serotonin releasing agents , αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses.[19] It is possible that αMT could cause the same neurotoxicity.
Legality [ edit ]
Australia [ edit ]
The 5-Methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.[20]
As of October 2015 αMT is a controlled substance in China.[21]
Denmark [ edit ]
In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances(List B).[22]
Canada has no mention of αMT in the Controlled Drugs and Substances Act .[23] However, αMT is on the Registration, Evaluation, Authorisation and Restriction of Chemicals(REACH) list of pre-registered substances as of March 2009.[22]
Germany [ edit ]
αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[22]
Austria [ edit ]
αMT is placed under Austrian law (NPSG) Group 6.[22]
Hungary [ edit ]
αMT was controlled on the Schedule C list in Hungary in 2013.[22]
Slovakia [ edit ]
αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[22]
Slovenia [ edit ]
αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[22]
Lithuania [ edit ]
In Lithuania (2012), αMT is controlled as a tryptamine derivative put under control in the 1st list of Narcotic Drugs and Psychotropic Substances which use is prohibited for medical purposes.[22]
αMT is legal in Spain.[24]
Sveriges riksdags health ministry Statens folkhälsoinstitut classified αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health ) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as alfa-metyltryptamin (AMT) , making it illegal to sell or possess.[25]
αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT .[26] This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.[27]
The Drug Enforcement Administration (DEA) placed αMT temporarily in schedule I of the Controlled Substances Act (CSA) on April 4, 2003, pursuant to the temporary scheduling provisions of the CSA (68 FR16427). On September 29, 2004, αMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).[28]
Finland [ edit ]
AMT, alfa-methyltryptamine is illegal in Finland[29]
Reported Deaths [ edit ]
Deaths from αMT are rare but as a powerful monoamine releaser injury can occur when excessive doses are taken or when taken with drugs such as MAOIs .[30] Most fatalities are not verified but those which are involve excessive doses[31] or coingestion with other drugs.[32] A British teenager died after consuming 1 g of αMT in August 2013.[33]
Synthesis [ edit ]
Prepn:[34] [35] [36] [37]
See also [ edit ]
^ MAOI potency was comparable at 7 µM/kg, equivalent to 1.5mg/kg of Harmaline and 1.2mg/kg of αMT. At 70µM/kg αMT was a much less effective MAOI than harmaline.[12]
References [ edit ]
^ a b c "Erowid AMT Vault : FAQ by Dialtonez" .
^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT" .
^ "Erowid AMT (alpha-methyltryptamine) Vault" .
^ US Patent 3296072 , Szmuszkovicz Jacob, "Method of Treating Mental Depression", published 1967-01-03, assigned to Upjohn Co
^ Donald G. Barceloux (20 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants . John Wiley & Sons. pp. 196–. ISBN 978-0-471-72760-6 .
^ Leslie Iversen (11 November 2013). Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man . Springer Science & Business Media. pp. 132–. ISBN 978-1-4613-4045-4 .
^ Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders . Academic Press. 17 May 2013. pp. 632–. ISBN 978-0-12-398360-2 .
^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain" . European Journal of Pharmacology . 559 (2-3): 132–7. doi :10.1016/j.ejphar.2006.11.075 . PMID 17223101 .
^ Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes" . Biological & Pharmaceutical Bulletin . 30 (12): 2328–33. doi :10.1248/bpb.30.2328 . PMID 18057721 .
^ Arai, Y.; Toyoshima, Y.; Kinemuchi, H. (1986). "Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. II. Inhibition by .ALPHA.-methylated substrate-analogue monoamines, .ALPHA.-methyltryptamine, .ALPHA.-methylbenzylamine and two enantiomers of .ALPHA.-methylbenzylamine". The Japanese Journal of Pharmacology . 41 (2): 191–197. doi :10.1254/jjp.41.191 .
^ Greig, M. E.; Walk, R. A.; Gibbons, A. J. (1959). "The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo" . The Journal of Pharmacology and Experimental Therapeutics . 127 : 110–115. PMID 13851725 .
^ a b Gey, K. F.; Pletscher, A. (1962). "Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo" . British journal of pharmacology and chemotherapy . 19 (1): 161–167. doi :10.1111/j.1476-5381.1962.tb01437.x . PMC 1482243 . PMID 13898151 .
^ "Shulgin, A (1997) TIHKAL " . Erowid.org. Retrieved 2013-10-16 .
^ "AMT Dosage" . Erowid . 2011-02-02. Retrieved 2013-10-16 .
^ Szara, S. (1961). "6-Hydroxylation: An important metabolic route for α-methyltryptamine". Experientia . 17 (2): 76–76. doi :10.1007/BF02171429 .
^ Kanamori, T.; Kuwayama, K.; Tsujikawa, K.; Miyaguchi, H.; Iwata, Y. T.; Inoue, H. (2008). "In vivometabolism of α-methyltryptamine in rats: Identification of urinary metabolites". Xenobiotica . 38 (12): 1476–1486. doi :10.1080/00498250802491654 . PMID 18982537 .
^ Wilcox, J. (2012). "Psychoactive Properties of Alpha-Methyltryptamine: Analysis from Self Reports of Users". Journal of Psychoactive Drugs . 44 (3): 274–276. doi :10.1080/02791072.2012.704592 . PMID 23061328 .
^ "Erowid AMT Vault : Effects" .
^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology . 200 (1): 187–90. doi :10.1016/0014-2999(91)90686-K . PMID 1722753 .
^ "Erowid 5-MeO-AMT Vault : Legal Status" .
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015 .
^ a b c d e f g h http://www.who.int/medicines/areas/quality_safety/4_20_Review.pdf
^ "CSDA" .
^ http://www.aemps.gob.es/medicamentosUsoHumano/estupefacientesPsicotropos/home.htm
^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" (pdf) , Lagen om förbud mot vissa hälsofarliga varor - SFS 2005:26 (in Swedish), February 2005, retrieved 2013-10-07
^ [1]
^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF) . UK Home Office. p. 12. Retrieved 10 June 2014 .
^ "ALPHA-METHYLTRYPTAMINE" (PDF) . DEA Office of Diversion Control . April 2013. Archived from the original on 2013-10-17. Retrieved 2013-10-10 .
^ http://www.finlex.fi/data/sdliite/liite/6194.pdf
^ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia . 95 (4): 434–441. doi :10.1093/bja/aei210 . PMID 16051647 . "drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers"
^ Boland, Diane M.; Andollo W; Hime GW; Hearn WL (July–August 2005). "Fatality Due to Acute Alpha-methyltryptamine Intoxication" (PDF) . Journal of Analytical Toxicology . 29 : 394–397. doi :10.1093/jat/29.5.394 . Retrieved October 1, 2013 .
^ "Call for ban on drug after reveller's death" . Western Gazette . March 22, 2012. Archived from the original on 2013-10-16. Retrieved October 1, 2013 .
^ "Southampton 'legal high' death deemed 'accidental' " . BBC News . 2013-11-12. Retrieved 2013-11-19 .
^ Snyder, H. R.; Katz, Leon (1947). "The Alkylation of Aliphatic Nitro Compounds with Gramine. A New Synthesis of Derivatives of Tryptamine1,2". Journal of the American Chemical Society . 69 (12): 3140–3142. doi :10.1021/ja01204a061 . ISSN 0002-7863 .
^ Ash, A. S. F.; Wragg, W. R. (1958). "790. Synthesis of the 3-2?-aminopropyl- and 3-2?-aminobutyl-derivatives of 5-hydroxyindole, and an alternative synthesis of 5-hydroxytryptamine". Journal of the Chemical Society (Resumed) : 3887. doi :10.1039/jr9580003887 . ISSN 0368-1769 .
^ Terzian, A. G.; Safrasbekian, R. R.; Sukasian, R. S.; Tatevosian, G. T. (15 November 1961). "Synthesis and some pharmacological properties of alpha-methyltryptamine and its 5-methoxy derivative". Experientia . 17 : 493–4. doi :10.1007/bf02158615 . PMID 13920395 .
^ Lloyd, David H.; Nichols, David E. (1986). "Nickel boride/hydrazine hydrate reduction of aromatic and aliphatic nitro compounds. Synthesis of 4-(benzyloxy)indole and .alpha.-alkyltryptamines". The Journal of Organic Chemistry . 51 (22): 4294–4295. doi :10.1021/jo00372a037 . ISSN 0022-3263 .
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Trazodone
Tricyclic antidepressants (e.g., amitriptyline )
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , haloperidol , loxapine , perphenazine , pimozide , pipamperone , prochlorperazine , thioridazine , thiothixene , trifluoperazine )
Volinanserin
Xylamidine
Yohimbine
5-HT2B
Agonists: 4-Methylaminorex
Aminorex
Amphetamines (eg., chlorphentermine , cloforex , dexfenfluramine , fenfluramine , levofenfluramine , norfenfluramine )
BW-723C86
DOx (e.g., DOB , DOC , DOI , DOM )
Ergolines (e.g., cabergoline , dihydroergocryptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
MDxx (e.g., MDA , MDMA , MDOH , MMDA )
Piperazines (e.g., mCPP )
PNU-22394
Ro60-0175
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , α-Me-5-HT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
5-HT2C
Agonists: 2Cs (e.g., 2C-B , 2C-E , 2C-I , 2C-T-2 , 2C-T-7 , 2C-T-21 )
5-Methoxytryptamines (5-MeO-DET , 5-MeO-DiPT , 5-MeO-DMT , 5-MeO-DPT , 5-MT )
α-Alkyltryptamines (e.g., 5-Cl-αMT , 5-Fl-αMT , 5-MeO-αET , 5-MeO-αMT , α-Me-5-HT , αET , αMT )
A-372159
AL-38022A
Alstonine
CP-809101
Dimemebfe
DOx (e.g., DOB , DOC , DOI , DOM )
Ergolines (e.g., ALD-52 , cabergoline , dihydroergotamine , ergine (LSA) , ergotamine , lisuride , LA-SS-Az , LSB , LSD , LSD-Pip , LSH , LSP , pergolide )
Flumexadol
Lorcaserin
MDxx (e.g., MDA , MDMA , MDOH , MMDA )
MK-212
Org 12962
Org 37684
Oxaflozane
PHA-57378
Phenethylamines (e.g., lophophine , mescaline )
Piperazines (e.g., aripiprazole , BZP , mCPP , quipazine , TFMPP )
PNU-22394
PNU-181731
Ro60-0175
Ro60-0213
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
Vabicaserin
WAY-629
WAY-161503
YM-348
Antagonists: Adatanserin
Agomelatine
Atypical antipsychotics (e.g., asenapine , clorotepine , clozapine , fluperlapine , iloperidone , melperone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , ziprasidone , zotepine )
Captodiame
CEPC
Cinanserin
Cyproheptadine
Deramciclane
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide , bromocriptine , LY-53857 , LY-215840 , mesulergine , metergoline , methysergide , sergolexole )
Etoperidone
Fluoxetine
FR-260010
Irindalone
Ketanserin
Ketotifen
Latrepirdine (dimebolin)
Medifoxamine
Metitepine (methiothepin)
Nefazodone
Pirenperone
Pizotifen
Propranolol
Ritanserin
RS-102221
S-14671
SB-200646
SB-206553
SB-221284
SB-228357
SB-242084
SB-243213
SDZ SER-082
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
TIK-301
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
5-HT3
Agonists: Alcohols (e.g., butanol , ethanol , trichloroethanol )
m-CPBG
Phenylbiguanide
Piperazines (e.g., BZP , mCPP , quipazine )
RS-56812
Serotonin (5-HT)
SR-57227
SR-57227A
Tryptamines (e.g., 2-Me-5-HT , 5-CT , bufotenidine (5-HTQ) )
Volatiles/gases (e.g., halothane , isoflurane , toluene , trichloroethane )
YM-31636
Antagonists: Alosetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
ICS-205930
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , mianserin , mirtazapine )
Thujone
Tropanserin
Tropisetron
Typical antipsychotics (e.g., loxapine )
Volatiles/gases (e.g., nitrous oxide , sevoflurane , xenon )
Vortioxetine
Zacopride
Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g., dihydroergocryptine , dihydroergotamine , ergotamine , lisuride , LSD , mesulergine , metergoline , methysergide )
Serotonin (5-HT)
Tryptamines (e.g., 2-Me-5-HT , 5-BT , 5-CT , 5-MT , Bufotenin , E-6801 , E-6837 , EMD-386088 , EMDT , LY-586713 , N-Me-5-HT , tryptamine )
WAY-181187
WAY-208466
Antagonists: ABT-354
Atypical antipsychotics (e.g., aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , iloperidone , olanzapine , tiospirone )
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12233
GW-742457
Idalopirdine
Ketanserin
Latrepirdine (dimebolin)
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro04-6790
Ro 63-0563
SB-258585
SB-271046
SB-357134
SB-399885
SB-742457
Tetracyclic antidepressants (e.g., amoxapine , mianserin )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g., amisulpride , aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , olanzapine , risperidone , sertindole , tiospirone , ziprasidone , zotepine )
Butaclamol
DR-4485
EGIS-12233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , imipramine )
Typical antipsychotics (e.g., acetophenazine , chlorpromazine , chlorprothixene , fluphenazine , loxapine , pimozide )
Vortioxetine