3412. DOM

Nomenclature

CAS number: 15588-95-1
2,5-Dimethoxy-α,4-dimethylbenzeneethanamine; 2,5-dimethoxy-α,4-dimethylphenethylamine; 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane; (±)-2,5-dimethoxy-4-methylamphetamine; STP.
C12H19NO2; mol wt 209.28.
C 68.87%, H 9.15%, N 6.69%, O 15.29%.

Description and references

Psychedelic compound of “hippie” culture. Prepn: A. T. Shulgin, US 3547999 (1970 to Dow). Pharmacology: B. T. Ho et al., J. Med. Chem. 13, 26 (1970). Clinical pharmacology: S. H. Snyder et al., Am. J. Psychiatry 125, 357 (1968). Mechanism of action: R. A. Glennon, Neuropsychopharmacology 3, 509 (1990); C. S. Aulakh et al., J. Pharmacol. Exp. Ther. 271, 143 (1994). Abuse potential: P. B. Silverman, B. T. Ho, Psychopharmacology 68, 209 (1980); D. Fiorella et al., ibid. 119, 239 (1995). Activity comparison of enantiomers: F. Benington et al., Nature 242, 185 (1973); sepn and determn of enantiomers by HPLC: J. Goto et al., J. Liq. Chromatogr. 2, 1179 (1979). Analysis by TLC: I. Ojanper"a et al., J. Planar Chromatogr. Mod. TLC 4, 373 (1991). Brief description including prepn: A. Shulgin, A. Shulgin, Pihkal (Transform Press, Berkeley CA, 1991) pp 637-642.

Chemical structure

Properties

mp 60.5-61°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 15589-00-1
C12H19NO2.HCl; mol wt 245.75.
C 58.65%, H 8.20%, N 5.70%, O 13.02%, Cl 14.43%.

Properties

White crystals from isopropanol/ether, mp 189-189.5°. LD50 i.p. in mice: 89 ±4.2 mg/kg (Ho).

Note

This is a controlled substance (hallucinogen): 21 CFR, 1308.11.