BOD (psychedelic)

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BOD
Clinical data
Other namesβ-Methoxy-2C-D; 4-Methyl-2,5,β-trimethoxyphenethylamine; β-MeO-2C-D
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action<30 minutes[1]
Duration of action8–16 hours[1]
Identifiers
  • 2-(2,5-dimethoxy-4-methylphenyl)-2-methoxyethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • COc1cc(C)c(cc1C(CN)OC)OC
  • InChI=1S/C12H19NO3/c1-8-5-11(15-3)9(6-10(8)14-2)12(7-13)16-4/h5-6,12H,7,13H2,1-4H3 checkY
  • Key:VTEIFHQUZWABDE-UHFFFAOYSA-N checkY
  (verify)

BOD, also known as 4-methyl-2,5,β-trimethoxyphenethylamine or as β-methoxy-2C-D, is a psychedelic drug of the phenethylamine, 2C, and BOx families.[1] It is the β-methoxy derivative of 2C-D.[1] The drug is taken orally.[1] BOD has been encountered as a novel designer drug.[2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BOD's dose range as 15 to 25 mg orally and its duration as 8 to 16 hours.[1] Its onset is within 30 minutes and peak effects occur within 1 hour or as late as 2 to 2.5 hours.[1]

The effects of BOD have been reported to include visual and contrast enhancement, closed-eye visuals, open-eye visuals, surroundings moving, no flowing of images, very little visual compared to certain other psychedelics, difficult to define mental effects, mood enhancement, pleasantness, religious feelings, enhanced conversation and conceptualization, relaxation, humor, little in the way of insights, and beautiful experience.[1] Other effects included strange discomfort, some queasiness, minimal to quite noticeable body load, tiredness, mental sluggishness, confusion, and sleep disruption.[1] One concluded that the "body price a bit too much for the mental effects".[1]

Interactions

Pharmacology

Pharmacodynamics

BOD shows high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 1.38 nM and 19.74 nM, respectively).[3] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3] The head-twitch response induced by BOD can be blocked by both the serotonin 5-HT2A receptor antagonist ketanserin and by the selective serotonin 5-HT2C receptor antagonist SB-242084, suggesting involvement of both the serotonin 5-HT2A and 5-HT2C receptors in BOD's psychedelic-like effects.[3] In addition to its psychedelic-like effects, BOD produces hypolocomotion and conditioned place preference (CPP) in rodents.[4] Conversely, it does not produce self-administration.[4] Similarly to other serotonergic psychedelics, BOD has been found to produce neurotoxicity in rodents.[3][5]

Chemistry

Synthesis

The chemical synthesis of BOD has been described.[1]

Analogues

Analogues of BOD include BOHD (β-hydroxy-2C-D) and BOB (β-methoxy-2C-B), among others.[1]

History

BOB was first described in the scientific literature by Alexander Shulgin, Peyton Jacob III, and Darrell Lemaire in 1985.[6] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1] It emerged as a novel designer drug by the 2010s.[2]

Society and culture

Canada

BOD is a controlled substance in Canada under phenethylamine blanket-ban language.[7]

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[8]

United States

BOD is unscheduled in the United States, but purchase, sale, or possession for human consumption could be prosecuted under the Federal Analogue Act.[9]

See also

References

  1. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. BOD Entry
  2. "BOD". АИПСИН (in Russian). Retrieved 7 January 2026.
  3. Custodio RJ, Ortiz DM, Lee HJ, Sayson LV, Kim M, Lee YS, Kim KM, Cheong JH, Kim HJ (July 2025). "Serotonin 2C receptors are also important in head-twitch responses in male mice". Psychopharmacology (Berl). 242 (7): 1585–1605. doi:10.1007/s00213-023-06482-9. PMID 37882810.
  4. Custodio RJ, Sayson LV, Botanas CJ, Abiero A, Kim M, Lee HJ, Ryu HW, Lee YS, Kim HJ, Cheong JH (September 2020). "Two newly-emerging substituted phenethylamines MAL and BOD induce differential psychopharmacological effects in rodents". J Psychopharmacol. 34 (9): 1056–1067. doi:10.1177/0269881120936458. PMID 32648801.
  5. Rudin D, Liechti ME, Luethi D (September 2021). "Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics". Exp Neurol. 343 113778. doi:10.1016/j.expneurol.2021.113778. PMID 34090893.
  6. Lemaire D, Jacob P, Shulgin AT (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". J Pharm Pharmacol. 37 (8): 575–577. doi:10.1111/j.2042-7158.1985.tb03072.x. PMID 2864422.
  7. "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  8. "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.
  9. "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2016-08-02