BOD

Effects

Euphoriaempathyinsightbrightened colourClosed/Open eye visualsenhanced tactile sensationmental/physical stimulationdecreased appetitepupil dilationrestlessnesschange in perceptionego softeningsweating/chillsmuscle tensionconfusioninsomnia TS

Shulgin notes

These figures come from the Shulgins' own small trials, published decades ago. They are history, not a dosing guide: they were never checked the way a harm reduction dose table is, and batches, purity and people differ.

Book

PiHKAL (1991), entry #14

Dose listed

15–25 mg orally WP

Duration listed

8–16 hours WP

Read entry #14 in Erowid's online library

From PiHKAL and TiHKAL by Alexander and Ann Shulgin, as tabulated in Wikipedia's articles on the books (CC BY-SA 4.0). The books' text belongs to the Shulgins, so only the listed figures and a link are given here. Synthesis details are never shown on this site.

Overview

Beta-methoxy analogue of 2C-D, seems to be more "mild" than the likes of 2C-X and DOX compounds. Is 50/50 whether the body load is barely there, or overpowering the experience. TS

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.[1][2] WP

History

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.[1][2][3] WP

Legal status

Canada

BOD is a controlled substance in Canada under phenethylamine blanket-ban language.[4] WP

United kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[5] WP

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.[6] WP

Pharmacology

Pharmacodynamics

BOD shows high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Kᵢ = 1.38 nM and 19.74 nM, 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.[7][8][9] WP

Chemistry

Formula

C12H19NO3 PC

CAS number

98537-41-8 PC

Molar mass (g/mol)

225.28 PC

IUPAC name (computed by PubChem)

2-(2,5-dimethoxy-4-methylphenyl)-2-methoxyethanamine PC

SMILES

CC1=CC(=C(C=C1OC)C(CN)OC)OC PC

InChIKey

VTEIFHQUZWABDE-UHFFFAOYSA-N PC

PubChem CID

44719486

Pop culture

No references added yet.

References

1. Harm reduction site BOD Entry CitePiHKAL
2. Other BOD
3. Journal / agency Lemaire D, Jacob P, Shulgin AT. Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J Pharm Pharmacol. August 1985. doi:10.1111/j.2042-7158.1985.tb03072.x · PMID 2864422
4. Other Controlled Drugs and Substances Act
5. Harm reduction site UK Misuse of Drugs act 2001 Amendment summary
6. Other 21 U.S. Code § 841 - Prohibited acts A
7. Journal / agency Custodio RJ, Ortiz DM, Lee HJ, Sayson LV, Kim M, Lee YS, Kim KM, Cheong JH, Kim HJ. Serotonin 2C receptors are also important in head-twitch responses in male mice. Psychopharmacology (Berl). July 2025. doi:10.1007/s00213-023-06482-9 · PMID 37882810
8. Journal / agency Custodio RJ, Sayson LV, Botanas CJ, Abiero A, Kim M, Lee HJ, Ryu HW, Lee YS, Kim HJ, Cheong JH. Two newly-emerging substituted phenethylamines MAL and BOD induce differential psychopharmacological effects in rodents. J Psychopharmacol. September 2020. doi:10.1177/0269881120936458 · PMID 32648801
9. Journal / agency Rudin D, Liechti ME, Luethi D. Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics. Exp Neurol. September 2021. doi:10.1016/j.expneurol.2021.113778 · PMID 34090893

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.