BOHD (drug)

BOHD
Clinical data
Other names	4-Methyl-2,5-dimethoxy-β-hydroxyphenethylamine; β-Hydroxy-2C-D; β-OH-2C-D
Routes of; administration	Oral
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 2-amino-1-(2,5-dimethoxy-4-methylphenyl)ethan-1-ol;
CAS Number	29348-16-1 ;
PubChem CID	44719489;
ChemSpider	21106263 ;
UNII	QX20VMP285;
CompTox Dashboard (EPA)	DTXSID70660352 ;
Chemical and physical data
Formula	C11H17NO3
Molar mass	211.261 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(C)c(cc1C(O)CN)OC;
	InChI InChI=1S/C11H17NO3/c1-7-4-11(15-3)8(9(13)6-12)5-10(7)14-2/h4-5,9,13H,6,12H2,1-3H3 ; Key:WCURBUJUIMRCCJ-UHFFFAOYSA-N ;
	(verify)

BOHD, also known as 4-methyl-2,5-dimethoxy-β-hydroxyphenethylamine or as β-hydroxy-2C-D, is a drug of the phenethylamine, 2C, and BOx families.^[1] It is the β-hydroxy derivative of 2C-D.^[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BOHD's dose as greater than 50 mg orally and its duration as unknown.^[1] Its effects have been reported to include a marked drop in blood pressure without any change in heart rate, suggestive of adrenolytic toxicity.^[1] Higher doses were not explored and other effects not observed or described.^[1]

Chemistry

Synthesis

The chemical synthesis of BOHD has been described.^[1]

Analogues

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

History

BOHD was first described in the scientific literature by Beng T. Ho and colleagues in 1970.^[2]^[3] Subsequently it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Legal status

Canada

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

United Kingdom

This substance is a Class A drug under the UK Misuse of Drugs Act 1971.^[5]

United States

In the United States, BOHD is a Schedule I isomer of mescaline.

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 833–834. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
^ Ho BT, Tansey LW, McIsaac WM (September 1970). "Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM)". Journal of Medicinal Chemistry. 13 (5): 1022. doi:10.1021/jm00299a071. PMID 5458353.
^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[Trachsel_2013-2] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 833–834. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.

[Ho_1970-3] Ho BT, Tansey LW, McIsaac WM (September 1970). "Derivatives of 2,5-dimethoxy-4-methylamphetamine (DOM)". Journal of Medicinal Chemistry. 13 (5): 1022. doi:10.1021/jm00299a071. PMID 5458353.

[CDSA-4] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[5] "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.

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