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TOMSO

Field	Value
verifiedrevid	470476429
image	TOMSO.svg
image_class	skin-invert-image
width	200px
routes_of_administration	Oral
class	Serotonergic psychedelic; Hallucinogen
ATC_prefix	None
duration_of_action	10–16 hours
CAS_number_Ref
CAS_number	757142-16-8
PubChem	15915373
ChemSpiderID_Ref
ChemSpiderID	21106387
UNII_Ref
UNII	7SW3C48M3B
synonyms	5-TOMSO; 5-TOM-sulfoxide; 2-Methoxy-4-methyl-5-methylsulfinylamphetamine
IUPAC_name	1-[5-(methanesulfinyl)-2-methoxy-4-methylphenyl]propan-2-amine
C	12	H=19	N=1	O=2	S=1
SMILES	COC1=C(C=C(C(=C1)C)S(=O)C)CC(C)N
StdInChI_Ref
StdInChI	1S/C12H19NO2S/c1-8-5-11(15-3)10(6-9(2)13)7-12(8)16(4)14/h5,7,9H,6,13H2,1-4H3
StdInChIKey_Ref
StdInChIKey	LMQLBXOYCGXTOM-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

TOMSO, or 5-TOMSO, also known as 2-methoxy-4-methyl-5-methylsulfinylamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx series. It is the analogue of DOM in which the methoxy group at the 5 position has been replaced with a sulfur-containing methylsulfinyl group.

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists TOMSO's dose as 150mg orally alone or 100 to 150mg orally in combination with alcohol and its duration as 10 to 16hours. TOMSO was reported to produce no or only threshold effects by itself at the assessed doses, but when alcohol was concomitantly ingested, clear hallucinogenic effects occurred. These effects included facial distortion and remarkable time dilation, among others. When combined with alcohol, "plus-two" and "plus-three" experiences occurred on the Shulgin Rating Scale.

The chemical synthesis of TOMSO has been described.

TOMSO was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.

References

{{CitePiHKAL [http://www.erowid.org/library/books_online/pihkal/pihkal173.shtml TOMSO entry]
(May 1983). "Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine". J Med Chem.

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methoxyphenethylamines phenol-ethers pihkal psychedelic-phenethylamines substituted-amphetamines sulfoxides thio-2cs-and--dox

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