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BOD (psychedelic)
| Field | Value | |||
|---|---|---|---|---|
| verifiedrevid | 401813792 | |||
| drug_name | BOD | |||
| image | 4-methyl-2,5,beta-trimethoxy-phenethylamine.svg | |||
| image_class | skin-invert-image | |||
| width | 225px | |||
| image2 | BOD-3d-sticks.png | |||
| image_class2 | bg-transparent | |||
| width2 | 200px | |||
| routes_of_administration | Oral | |||
| class | Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen | |||
| ATC_prefix | None | |||
| duration_of_action | 8–16 hours | |||
| CAS_number_Ref | ||||
| CAS_number | 98537-41-8 | |||
| PubChem | 44719486 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 21106262 | |||
| UNII_Ref | ||||
| UNII | 9PXE981731 | |||
| synonyms | β-Methoxy-2C-D; 4-Methyl-2,5,β-trimethoxyphenethylamine; β-MeO-2C-D | |||
| IUPAC_name | 2-(2,5-dimethoxy-4-methylphenyl)-2-methoxyethan-1-amine | |||
| C | 12 | H=19 | N=1 | O=3 |
| SMILES | COc1cc(C)c(cc1C(CN)OC)OC | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | VTEIFHQUZWABDE-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life =
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. It is the β-methoxy derivative of 2C-D. The drug is taken orally. BOD has been encountered as a novel designer drug.
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BOD's dose range as 15 to 25mg orally and its duration as 8 to 16hours. 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.
Interactions
Pharmacology
Pharmacodynamics
BOD shows high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 1.38nM and 19.74nM, respectively). It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. 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. In addition to its psychedelic-like effects, BOD produces hypolocomotion and conditioned place preference (CPP) in rodents. Conversely, it does not produce self-administration. Similarly to other serotonergic psychedelics, BOD has been found to produce neurotoxicity in rodents.
Chemistry
Synthesis
The chemical synthesis of BOD has been described.
Analogues
Analogues of BOD include BOHD (β-hydroxy-2C-D) and BOB (β-methoxy-2C-B), among others.
History
BOB was first described in the scientific literature by Alexander Shulgin, Peyton Jacob III, and Darrell Lemaire in 1985. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). It emerged as a novel designer drug by the 2010s.
Society and culture
Legal status
Canada
BOD is a controlled substance in Canada under phenethylamine blanket-ban language.
United Kingdom
This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.
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.
References
References
- "BOD".
- {{CitePiHKAL [http://www.erowid.org/library/books_online/pihkal/pihkal014.shtml BOD Entry]
- (July 2025). "Serotonin 2C receptors are also important in head-twitch responses in male mice". Psychopharmacology (Berl).
- (September 2020). "Two newly-emerging substituted phenethylamines MAL and BOD induce differential psychopharmacological effects in rodents". J Psychopharmacol.
- (September 2021). "Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics". Exp Neurol.
- (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". J Pharm Pharmacol.
- "Controlled Drugs and Substances Act".
- "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design.
- "21 U.S. Code § 841 - Prohibited acts A".
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