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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
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

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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 reported effects include mild open-eye and moderate closed-eye visual changes, enhancement of conversation and sense of humor, and unpleasant physical effects such as nausea and lethargy.[1]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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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

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Synthesis

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

Analogues

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

History

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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

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Canada

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

United Kingdom

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

United States

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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

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References

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  1. ^ a b c d e f g h i j 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. ^ a b "BOD". АИПСИН (in Russian). Retrieved 7 January 2026.
  3. ^ a b c d 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. ^ a b 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
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