DMHP.Dimethylheptylpyran

DMHP is a classical cannabinoid: it retains the tricyclic skeleton of THC and modifies only two points, the position of the double bond, at 6a,10a, and the side chain, a branched 1,2-dimethylheptyl group replacing the pentyl. In animals it reproduces effects of Δ9-THC: a dose-dependent slowing of cortical somatosensory responses in the cat, where it is more potent than THC (Wilkison et al., 1982), a fall in temperature in the cat and tachycardia in the awake rat. What separates it most clearly from THC is cardiovascular: Pradhan's review (1984) concludes that it has a more potent and more prolonged hypotensive action than Δ9-THC for a much lesser psychic effect, with orthostatic hypotension at doses far below those causing mild mental incapacitation. DMHP and its acetate (EA-2233) have similar potency, and each consists of eight stereoisomers of unequal potency: isomers 2 and 4 are the most active. The activity is attributed to the CB1 receptor without any binding constant or measure of efficacy having been published for this compound, its pharmacology having been established before the identification of the receptors. A study of the effects and disposition of DMHP in humans was published in 1974 (Lemberger et al.); the sources consulted describe no clinical trial.

Source

An entirely synthetic molecule, absent from cannabis and from any living organism: no plant produces it. Described as early as 1949 in the work of Roger Adams on tetrahydrocannabinol analogues, it was later studied in the 1960s by the American military programme of incapacitating agents at Edgewood Arsenal, which gave it the designations EA-1476 (DMHP) and EA-2233 (its O-acetyl ester). The sources consulted do not report it in any consumer product, and it enters into no legal hemp-based product.

No biological pathway. Dimethylheptylpyran results from no biosynthesis: there is no living precursor bearing a 1,2-dimethylheptyl chain, and the molecule belongs solely to synthetic chemistry, without any enzymatic step.

European Union

The substance is not listed in the Annex to Council Framework Decision 2004/757/JHA (consolidated version of 12 January 2026), which lists the new psychoactive substances controlled at European Union level; control is a matter for national law. DMHP appears in Schedule I of the 1971 Convention on Psychotropic Substances (green list of the International Narcotics Control Board, 35th and 36th editions), to which the member states are parties; it is classified in national legislation, with categories and penalty regimes that vary from one country to another and must be checked locally.

France

Classified as a narcotic in France, and designated by name: the consolidated list published by the ANSM carries the entry « DMHP ou hydroxy-1 (diméthyl-1,2 heptyl)-3 tétrahydro-7,8,9,10 triméthyl-6,6,9 6H-dibenzo(b,d)pyranne », listed by the decree of 22 February 1990, amended on this point by the decree of 24 March 2000, and placed in annex III, the one that reproduces Schedules I and II of the 1971 Convention on Psychotropic Substances. It is therefore not a capture by the generic clause covering tetrahydrocannabinols, their esters, their ethers and their salts: the substance is targeted in its own right. The asterisk preceding the entry extends the classification to its stereoisomers, which matters here since DMHP exists as eight stereoisomers of unequal potency (Pradhan, 1984); its salts are covered. Production, possession, use, transfer and importation are prohibited.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Family

Synthetic CB receptor agonist › Research ligand or medicine

Class

classical

Verification

Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.

Wikipedia (English)

Dimethylheptylpyran (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

1. 1Adams R, Harfenist M, Loewe S. New Analogs of Tetrahydrocannabinol. XIX. J Am Chem Soc. 1949;71(5):1624-1628 (new tab)DOI 10.1021/ja01173a023
2. 2Pradhan SN. Pharmacology of some synthetic tetrahydrocannabinols. Neurosci Biobehav Rev. 1984;8(3):369-385 (review devoted to DMHP and its acetate: EA 1476, EA 2233, orthostatic hypotension, eight isomers) (new tab)PMID 6095152
3. 3Valenzuela-Tapia LN et al. The Blurred Lines Between New Psychoactive Substances and Potential Chemical Weapons. Toxics. 2025 (EA-2233, the O-acetyl ester of DMHP; Edgewood Arsenal) (new tab)PMID 40863935
4. 4Lemberger L, McMahon R, Archer R, Matsumoto K, Rowe H. Pharmacologic effects and physiologic disposition of delta 6a,10a dimethyl heptyl tetrahydrocannabinol (DMHP) in man. Clin Pharmacol Ther. 1974;15(4):380-386 (new tab)PMID 4821441
5. 5Lemberger L, McMahon RE, Archer R, Matsumoto K, Rowe H. The in vitro and in vivo metabolism of delta 6a,10a dimethyl heptyl tetrahydrocannabinol (DMHP). J Pharmacol Exp Ther. 1973;187(1):169-175 (new tab)PMID 4746325
6. 6Osgood PF, Howes JF. delta9-Tetrahydrocannabinol and dimethylheptylpyran induced tachycardia in the conscious rat. Life Sci. 1977 (new tab)PMID 927033
7. 7Wilkison DM, Pontzer N, Hosko MJ. Slowing of cortical somatosensory evoked activity by delta 9-tetrahydrocannabinol and dimethylheptylpyran in alpha-chloralose-anesthetized cats. Neuropharmacology. 1982;21(7):705-709 (new tab)PMID 6289158
8. 8Hosko MJ, Schmeling WT, Hardman HF. Evidence for a caudal brainstem site of action for cannabinoid induced hypothermia. Brain Res Bull. 1981 (DMHP studied with THC and 11-OH-THC) (new tab)PMID 7225905
9. 9ANSM, consolidated list of substances classified as narcotics, updated 16 February 2026 (Annex III, entry « DMHP ou hydroxy-1 (diméthyl-1,2 heptyl)-3 tétrahydro-7,8,9,10 triméthyl-6,6,9 6H-dibenzo(b,d)pyranne ») (new tab)
10. 10Order of 22 February 1990 setting the list of substances classified as narcotics, Légifrance (new tab)
11. 11INCB, Green List of psychotropic substances under international control, 35th edition, 2024 (Schedule I: DMHP) (new tab)
12. 12INCB, Green List of psychotropic substances under international control, 36th edition, 2025 (Schedule I: DMHP) (new tab)
13. 13PubChem, Compound Summary CID 36276, 3-(1,2-dimethylheptyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo(b,d)pyran-1-ol (identifiers and formula) (new tab)

SMILES

CCCCCC(C)C(C)C1=CC2=C(C3=C(CCC(C3)C)C(O2)(C)C)C(=C1)O

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.