MBM (drug)

MBM, also known as 2,5-dimethoxy-4-butoxyamphetamine or as TMA2-4-BuO, is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.^[1]^[2]^[3] It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended.^[1]^[2]^[3] According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), MBM produced no effects at doses of up to 12 mg orally.^[1]^[2]^[3]^[4] Higher doses were not tested.^[1]^[2]^[3] As such, the properties and effects of MBM remain unknown.^[1]^[2]^[3] The drug is a potent full agonist of the serotonin 5-HT_2A and 5-HT_2C receptors (EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) = 26.9 nM (114%) and 57.4 nM (93%), respectively).^[5] Conversely, it is inactive as an agonist of the serotonin 5-HT_2B and 5-HT_1A receptors.^[5] The chemical synthesis of MBM has been described.^[1]^[5] MBM was first described in the literature by Shulgin in PiHKAL in 1991.^[1]^[2]

Other names4-Butoxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-butoxyamphetamine; TMA2-4-BuO

Routes of
administrationOral^[1]^[2]^[3]

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist

ATC code

None

Quick facts Clinical data, Other names ...

MBM
Clinical data

Other names	4-Butoxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-butoxyamphetamine; TMA2-4-BuO
Routes of administration	Oral^[1]^[2]^[3]
Drug class	Serotonin receptor modulator; Serotonin 5-HT_2A receptor agonist
ATC code	None
Pharmacokinetic data
Duration of action	Unknown^[1]^[2]^[3]
Identifiers
IUPAC name 1-(4-butoxy-2,5-dimethoxyphenyl)propan-2-amine
PubChem CID	69456028
ChemSpider	129687355
Chemical and physical data
Formula	C₁₅H₂₅NO₃
Molar mass	267.369 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCOC1=C(C=C(C(=C1)OC)CC(C)N)OC
InChI InChI=1S/C15H25NO3/c1-5-6-7-19-15-10-13(17-3)12(8-11(2)16)9-14(15)18-4/h9-11H,5-8,16H2,1-4H3 Key:QKAUNHGCSPPQBX-UHFFFAOYSA-N

References

[1]
Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The extension of the 4-alkoxy-group led to the discovery of the TMA-2—MEM—MIPM—MPM—MBM series of amphetamine analogues. The 2-carbon counterparts of these would be a fascinating series to explore, I thought, if there was some encouragement to be had from a preliminary try in this field." [...] "These are the exact analogues of 2C-T-2, 2C-T-7, and 2C-T-19, resp., and the 2-carbon homologues of MEM, MPM, and MBM." [...] "Three additional materials of this pattern were prepared and either shown to be even less active, or simply were not assayed at all. These are the 4-isopropoxy isomer (MIPM), the n-butoxy homologue (MBM), and the n-amyl homologue (MAM). They scarcely warrant separate recipes as they were all made in a manner similar to this one describing MPM." [...] "For the preparation of MBM, the starting phenol was alkylated to 2-n-butoxy-1,4-dimethoxybenzene in methanolic KOH with n-butyl bromide. The benzaldehyde melted at 79.5–81 °C from methanol, and formed a malononitrile derivative that had a melting point of 134.5–135 °C. The nitrostyrene from the aldehyde and nitroethane in acetic acid crystallized from methanol with a mp of 71–72 °C. Lithium aluminum hydride reduction in ether gave the ether-insoluble chloroform-soluble product 4-n-butoxy-2,5-dimethoxyamphetamine hydrochloride (MBM) with a melting point of 128–130 °C. This product met all tests for structural integrity, and assays were started. At levels of up to 12.0 milligrams, there were no effects noted."
[2]
Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
[3]
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. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
[4]
Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Frontiers in Pharmacology. 10 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671. Although the 2C-O derivatives initially examined by Shulgin were shown to be fairly inactive in humans (2C-O-1; 21 and 2C-O-4; 22, Figure 3) some derivatives such as 19 and 2,5-dimethoxy-4-ethoxyamphetamie (MEM) (24) displayed psychedelic activity (Figure 3) (Shulgin and Shulgin, 1991). However, upon further increasing chain length to a 4-propyloxy (MPM; 26) or 4-butyloxy (MBM; structure not shown) substituent, again no psychoactive effects could be observed on comparable doses as used for 19 and 24. The rather mixed results of low human potency and inactivity was one of the reasons Shulgin did not further evaluate the structure-activity relationship (SAR) of the 2C-O and 3C-O derivatives.
[5]
WO 2022192781A1, Kruegel AC, "Phenalkylamines and methods of making and using the same", published 15 September 2022, assigned to Gilgamesh Pharmaceuticals Inc.

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