Charmian (drug)

Charmian
Clinical data
Other namesCHARMIAN; α-Methyl-DOM; α-Me-DOM; BL-4041A; BL4041A; α,α,4-Trimethyl-2,5-dimethoxyphenethylamine; Phentermine-DOM
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1-(2,5-dimethoxy-4-methylphenyl)-2-methylpropan-2-amine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H21NO2
Molar mass223.316 g·mol−1
3D model (JSmol)
  • CC1=CC(=C(C=C1OC)CC(C)(C)N)OC
  • InChI=1S/C13H21NO2/c1-9-6-12(16-5)10(7-11(9)15-4)8-13(2,3)14/h6-7H,8,14H2,1-5H3
  • Key:CETRTEFIJATLFR-UHFFFAOYSA-N

Charmian, also known as α-methyl-DOM, α,α,4-trimethyl-2,5-dimethoxyphenethylamine, or BL-4041A, is a serotonin receptor modulator of the phenethylamine, amphetamine, phentermine, and DOx families related to DOM.[1][2][3][4] It is the α-methyl derivative of DOM or the 4-methyl-2,5-dimethoxy derivative of phentermine.[1][2][3][4] According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), Charmian was synthesized and studied and was found to be of greatly reduced affinity for serotonin receptors and potency in animals compared to DOM.[1][3][4] It is not known to have been tested in humans.[1] The drug is one of Shulgin's "ten classic ladies", a series of methylated DOM derivatives.[1][2] The chemical synthesis of Charmian has been described.[4] Charmian was first described in the scientific literature by C. F. Barfknecht and colleagues in 1978.[4] The drug is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of DOET.[5][6]

See also

References

  1. ^ a b c d e Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "Replacing the alpha-hydrogen of DOM with a methyl group would give the phentermine analogue which is named CHARMIAN. You may be thinking of Cleopatra’s favorite attendant, but I was thinking of the sweet wife of a very dear friend of mine, a lady who has been in a state of gentle schizophrenia for some forty years now. The MDA analogue of CHARMIAN has been described in this foornote under the code name of MDPH. CHARMIAN, herself, has been synthesized and is of very much reduced potency in animals, as compared to DOM. It has not been tried in man as far as I know."
  2. ^ a b c Ger A, Ger D. "Triple Goddess of the Night". British Neuroscience Association Bulletin. 63: 28–30.
  3. ^ a b c Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. Bibcode:1981JPhmS..70..839N. doi:10.1002/jps.2600700802. PMID 7031221.
  4. ^ a b c d e Barfknecht, CF; Caputo, JF; Tobin, MB; Dyer, DC; Standridge, RT; Howell, HG; Goodwin, WR; Partyka, RA; Gylys, JA; Cavanagh, RL. (1978). Congeners of DOM: Effect of distribution on the evaluation of pharmacologic data. QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22. https://isomerdesign.com/bitnest/external/Books/NIDA22.16
  5. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  6. ^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.
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