2,6-Dimethoxyamphetamine

2,6-Dimethoxyamphetamine (2,6-DMA), also known as DMA-5, is a drug of the phenethylamine and amphetamine families.^[1] It is one of the positional isomers of dimethoxyamphetamine.^[1]

2,6-Dimethoxyamphetamine

Clinical data
Other names	2,6-DMA; DMA-5
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 1-(2,6-dimethoxyphenyl)propan-2-amine
CAS Number	23690-14-4
PubChem CID	141048
ChemSpider	124412
UNII	GCG9F6BC2R
ChEMBL	ChEMBL30577
CompTox Dashboard (EPA)	DTXSID40946493
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=C(C=CC=C1OC)OC)N
InChI InChI=1S/C11H17NO2/c1-8(12)7-9-10(13-2)5-4-6-11(9)14-3/h4-6,8H,7,12H2,1-3H3 Key:OHGNLLDQBKOWJW-UHFFFAOYSA-N

The drug showed very low affinity for serotonin receptors in rat stomach fundus strips (A₂ = 8,130 nM).^[1][2] In a subsequent study, it showed no affinity for the serotonin 5-HT_2A or 5-HT_2C receptors (K_i = >10,000 nM).^[3] 2,6-DMA only partially substituted for DOM in rodent drug discrimination tests, with a maximum responding of 41% and behavioral disruption at higher doses.^[4][5] It did not substitute for dextroamphetamine in these tests.^[5][6] The drug has not been tested in humans and its effects in humans are unknown.^[1]

2,6-DMA was first described in the scientific literature by Alexander Shulgin by 1969.^[7] At that time, he had not yet synthesized it and did not report its effects.^[7] 2,6-DMA is a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA) and hence is a Schedule I controlled substance in the United States.^[1]

See also

• Substituted methoxyphenethylamine
• Dimethoxyamphetamine
• 2,6-Dimethoxyphenethylamine

References

1. Shulgin A, Manning T, Daley PF (2011). "#34. 2,3-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 51–54. ISBN 978-0-9630096-3-0. OCLC 709667010.
2. Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
3. Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". J Med Chem. 43 (16): 3074–3084. doi:10.1021/jm9906062. PMID 10956215.
4. Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
5. Glennon RA (June 1986). "Discriminative stimulus properties of phenylisopropylamine derivatives". Drug Alcohol Depend. 17 (2–3): 119–134. doi:10.1016/0376-8716(86)90003-7. PMID 2874967.
6. Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.
7. Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297.

External links

• 2,6-DMA - Isomer Design