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Α,N,O-TMS

Chemical compound

Field	Value
drug_name	α,N,O-TMS
verifiedrevid	399498190
image	A,N,O-TMS.svg
image_class	skin-invert-image
width	225px
image2	Α,N,O-TMS 3D.png
image_class2	bg-transparent
width2	200px
pregnancy_AU
pregnancy_US
routes_of_administration	Oral
ATC_prefix	None
legal_AU
legal_CA
legal_UK
legal_US
duration_of_action	6–8 hours
CAS_number_Ref
CAS_number	4822-13-3
UNII_Ref
UNII	PJ8WT93MNQ
PubChem	20961
DrugBank_Ref
ChemSpiderID_Ref
ChemSpiderID	19718
synonyms	α,N,O-Trimethylserotonin; α,N,O-TMS; 5-Methoxy-α,N-dimethyltryptamine; 5-MeO-α,N-DMT; 5-MeO-α-Me-NMT; N-Methyl-5-MeO-AMT; 5-MeO-ADMT
IUPAC_name	1-(5-methoxy-1H-indol-3-yl)propan-2-ylamine
C	13	H=18	N=2	O=1
SMILES	O(c1cc2c(cc1)[nH]cc2CC(NC)C)C
StdInChI_Ref
StdInChI	1S/C13H18N2O/c1-9(14-2)6-10-8-15-13-5-4-11(16-3)7-12(10)13/h4-5,7-9,14-15H,6H2,1-3H3
StdInChIKey_Ref
StdInChIKey	IYEMYZOLBLHKFE-UHFFFAOYSA-N

| elimination_half-life =

α,N,O-Trimethylserotonin (α,N,O-TMS), also known as 5-methoxy-α,N-dimethyltryptamine (5-MeO-α,N-DMT), is a psychedelic drug of the tryptamine and α-alkyltryptamine families. It is taken orally.

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Shulgin lists the dose as 10 to 20mg orally and the duration as 6 to 8hours. The drug is significantly less potent than its non-N-methylated parent compound 5-MeO-AMT (5-methoxy-α-methyltryptamine), which has a dose range of 2.5 to 4.5mg and a duration of 12 to 18hours.

Interactions

Chemistry

Synthesis

The chemical synthesis of α,N,O-TMS has been described.

Analogues

Analogues of α,N,O-TMS (N-methyl-5-MeO-AMT) include α-methyltryptamine (AMT), α,N-DMT (N-methyl-AMT), α,N,N-TMT (N,N-dimethyl-AMT), α-methylserotonin (AMS; 5-HO-AMT), 5-MeO-AMT (α,O-DMS), and α,N,N,O-TeMS (N,N-dimethyl-5-MeO-AMT), among others.

References

(24 April 2003). "α,N,O-TMS (5-MeO-ADMT)".
{{CiteTiHKAL

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alpha-alkyltryptamines 5-methoxytryptamines n-monoalkyltryptamines psychedelic-tryptamines tihkal

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