BOHH

BOHH
Clinical data
Other names3,4-Methylenedioxy-β-hydroxyphenethylamine; β-Hydroxy-3,4-methylenedioxyphenethylamine; β-Hydroxy-MDPEA; Methylenedioxyethanolamine; MDE
Routes of
administration		Oral
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown
Identifiers
  • 2-amino-1-(1,3-benzodioxol-5-yl)ethanol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC9H11NO3
Molar mass181.191 g·mol−1
3D model (JSmol)
  • C1OC2=C(O1)C=C(C=C2)C(CN)O
  • InChI=1S/C9H11NO3/c10-4-7(11)6-1-2-8-9(3-6)13-5-12-8/h1-3,7,11H,4-5,10H2
  • Key:NFDJYUZZSPJWLV-UHFFFAOYSA-N

BOHH, also known as 3,4-methylenedioxy-β-hydroxyphenethylamine or as β-hydroxy-MDPEA, is a chemical compound of the phenethylamine, MDxx, and BOx families related to 3,4-methylenedioxyphenethylamine (MDPEA). It is the β-hydroxy derivative of MDPEA and the β-O-desmethyl analogue of BOH (β-methoxy-MDPEA). The drug is also the 3,4-methylenedioxy analogue of the neurotransmitter norepinephrine.

According to Alexander Shulgin in his book Phenethylamines I Have Known and Loved (PiHKAL) and other publications, BOHH is inactive at doses of up to 100 mg orally. On the other hand, Michael Valentine Smith claimed in his book Psychedelic Chemistry that BOHH "is said to be a very fine trip", with no other information provided.

BOHH was first described in the scientific literature by at least 1981. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.

See also

References

  1. 1 2 3 4 5 6 7 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The demethylated homologue of BOH is BOHH, and is the methylenedioxy analogue of norepinephrine. It might well hydrolytically open up in the body to provide this neurotransmitter, and serve as some sort of transmitter in its own right. It is discussed under DME." [...] "There, a reasonable code name for this specific compound is given, namely BOHH. “BO” stands for the beta-oxygen function on a phenethylamine; this is the heart of the BOX family. The “H” which is the third letter of BOHH stands for the free hydroxyl group. And the final “H” is for homopiperonylamine (which is the trivial name for the compound without the hydroxyl group). BOHH, or 3,4-methylenedioxy-β-hydroxyphenethylamine, or 3,4-methylenedioxy-β-ethanolamine, has also been assayed in man at up to 100 milligrams without any effects, and must be considered, as of now, to be inactive centrally. The possible toxic roles of beta-ethanolamines as potential adrenolytic agents, have been discussed in the BOHD recipe. And beware of the use of the code name MDE in the very old literature. It might be this BOHH compound." [...] "The beta-hydroxy analogue of MDPEA is the ethanolamine MDE, standing for methylenedioxyethanolamine. This is an old term, and in the more recent literature, since 1975 certainly, MDE has been used to represent methylenedioxyethylamphetamine."
  2. 1 2 3 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. The analogous derivative of BOH is 3,4-methylenedioxyphenyl-β-ethanolamine (BOHH). In the early literature it is occasionally referred to by the name MDE but this code has now been exclusively assigned to the N-ethyl homologue of MDMA. It is inactive at an oral dosage of 100mg. The corresponding dimethoxy compound (3,4-dimethoxyphenyl-ẞ-ethanolamine, DME) has been studied at doses of up to 115mg and is without psychoactivity.
  3. 1 2 Smith MV (1981). "Mescaline and Friends". Psychedelic Chemistry. Loompanics Unlimited. p. 77. ISBN 978-0-915179-10-7. Beta-hydroxy-3,4-methylenedioxyphenylethyl amine is said to be a very fine trip.