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It was invented in&nbsp;1949 during attempts to elucidate the structure of Δ<sup>9</sup>-THC, one of the active components of [[Cannabis (drug)|cannabis]].<ref>{{cite journal|vauthors=Adams R, Harfenist M, Loewe S |doi=10.1021/ja01173a023|year=1949|journal=Journal of the American Chemical Society|title = New Analogs of Tetrahydrocannabinol. XIX| volume=71|issue=5|pages=1624–1628}}</ref> DMHP is a pale yellow, viscous oil which is insoluble in water but dissolves in alcohol or non-polar solvents. DMHP is similar in structure to THC, differing only in the position of one double bond, and the replacement of the 3-pentyl chain with a 3-(1,2-dimethylheptyl) chain.<ref>{{cite book |url=https://archive.org/details/totalsynthesisof03john |title=Total Synthesis of Natural Products |vauthors=Razdan RK |publisher=Wiley-Interscience |year=1980 |isbn=978-0-471-05460-3 |volume=4 |pages=185–262 |chapter=The Total Synthesis of Cannabinoids |doi=10.1002/9780470129678.ch2 |url-access=registration}}</ref> ==Effects== DMPH produces similar activity to THC, such as [[sedative]] effects, but is considerably more potent,<ref>{{cite journal | vauthors = Wilkison DM, Pontzer N, Hosko MJ | title = Slowing of cortical somatosensory evoked activity by delta 9-tetrahydrocannabinol and dimethylheptylpyran in alpha-chloralose-anesthetized cats | journal = Neuropharmacology | volume = 21 | issue = 7 | pages = 705–9 | date = July 1982 | pmid = 6289158 | doi = 10.1016/0028-3908(82)90014-4 | s2cid = 35663464 }}</ref> especially having much stronger [[analgesic]] and [[anticonvulsant]] effects than THC, although comparatively weaker psychological effects. == Mechanism of action == It is thought to act as a [[Cannabinoid receptor|CB<sub>1</sub> receptor]] [[agonist]], in a similar manner to other [[cannabinoid]] derivatives.<ref name="pmid817021">{{cite journal | vauthors = Winn M, Arendsen D, Dodge P, Dren A, Dunnigan D, Hallas R, Hwang K, Kyncl J, Lee YH, Plotnikoff N, Young P, Zaugg H | title = Drugs derived from cannabinoids. 5. delta6a,10a-Tetrahydrocannabinol and heterocyclic analogs containing aromatic side chains | journal = Journal of Medicinal Chemistry | volume = 19 | issue = 4 | pages = 461–71 | date = April 1976 | pmid = 817021 | doi = 10.1021/jm00226a003 }}</ref><ref>{{cite journal | vauthors = Parker LA, Mechoulam R | title = Cannabinoid agonists and antagonists modulate lithium-induced conditioned gaping in rats | journal = Integrative Physiological and Behavioral Science | volume = 38 | issue = 2 | pages = 133–45 | year = 2003 | pmid = 14527182 | doi = 10.1007/BF02688831 | s2cid = 38974868 }}</ref> While DMHP itself has been subject to relatively little study since the characterization of the cannabinoid receptors, the structural isomer 1,2-dimethylheptyl-Δ<sup>8</sup>-THC has been shown to be a highly potent cannabinoid agonist, and the activity of its enantiomers has been studied separately.<ref>{{cite journal | vauthors = Huffman JW, Duncan Jr SG, Wiley JL, Martin BR | title = Synthesis and pharmacology of the 1′,2′-dimethylheptyl-Δ8-THC isomers: exceptionally potent cannabinoids. | journal = Bioorganic & Medicinal Chemistry Letters | date = 1997 | volume = 7 | issue = 21 | pages = 2799–2804 | doi = 10.1016/S0960-894X(97)10086-5 }}</ref> ==Chemistry== === Isomerism === [[File:Dibenzopyran and monoterpenoid numbering of tetrahydrocannabinol.svg|center|300px|Dibenzopyran and monoterpenoid numbering of tetrahydrocannabinol derivatives]] {| class="wikitable" style="clear:left" |- ! colspan="10" | 7 double bond isomers of dimethylheptylpyran and their 120 stereoisomers |- ! colspan="3" | Dibenzopyran numbering !! colspan="2" | Monoterpenoid numbering !! colspan="2" | Additional chiral centers on side chain !! rowspan="2" | Number of stereoisomers !! rowspan="2" | Natural occurrence !! rowspan="2" | [[Convention on Psychotropic Substances]] Schedule |- ! Short name !! Chiral centers in dibenzopyran backbone !! Full name !! Short name !! Chiral centers in dibenzopyran backbone !! 1,2-dimethylheptyl numbering !! 3-methyloctan-2-yl numbering |- | Δ<sup>6a(7)</sup>-DMHP || 9 and 10a || 3-(1,2-dimethylheptyl)-8,9,10,10a-tetrahydro-6,6,9-trimethyl-6''H''-dibenzo[''b'',''d'']pyran-1-ol || Δ<sup>4</sup>-DMHP || 1 and 3 || 1 and 2 || 2 and 3 || 16 || No || unscheduled |- | Δ<sup>7</sup>-DMHP || 6a, 9 and 10a || 3-(1,2-dimethylheptyl)-6a,9,10,10a-tetrahydro-6,6,9-trimethyl-6''H''-dibenzo[''b'',''d'']pyran-1-ol || Δ<sup>5</sup>-DMHP || 1, 3 and 4 || 1 and 2 || 2 and 3 || 32 || No || unscheduled |- | Δ<sup>8</sup>-DMHP || 6a and 10a || 3-(1,2-dimethylheptyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6''H''-dibenzo[''b'',''d'']pyran-1-ol || Δ<sup>6</sup>-DMHP || 3 and 4 || 1 and 2 || 2 and 3 || 16 || No || unscheduled |- | Δ<sup>9,11</sup>-DMHP || 6a and 10a || 3-(1,2-dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-9-methylene-6''H''-dibenzo[''b'',''d'']pyran-1-ol || Δ<sup>1(7)</sup>-DMHP || 3 and 4 || 1 and 2 || 2 and 3 || 16 || No || unscheduled |- | Δ<sup>9</sup>-DMHP || 6a and 10a || 3-(1,2-dimethylheptyl)-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-6''H''-dibenzo[''b'',''d'']pyran-1-ol || Δ<sup>1</sup>-DMHP || 3 and 4 || 1 and 2 || 2 and 3 || 16 || No || unscheduled |- | Δ<sup>10</sup>-DMHP || 6a and 9 || 3-(1,2-dimethylheptyl)-6a,7,8,9-tetrahydro-6,6,9-trimethyl-6''H''-dibenzo[''b'',''d'']pyran-1-ol || Δ<sup>2</sup>-DMHP || 1 and 4 || 1 and 2 || 2 and 3 || 16 || No || unscheduled |- | '''Δ<sup>6a(10a)</sup>-DMHP''' || '''9''' || '''3-(1,2-dimethylheptyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6''H''-dibenzo[''b'',''d'']pyran-1-ol''' || '''Δ<sup>3</sup>-DMHP''' || '''1''' || '''1 and 2''' || '''2 and 3''' || '''8''' || '''No''' || '''Schedule I''' |} Note that 6''H''-dibenzo[''b'',''d'']pyran-1-ol is the same as 6''H''-benzo[''c'']chromen-1-ol. == History == === Edgewood Arsenal and EA-2233 === The fiscal budgeting and planning for Edgewood Arsenal (established in 1948) considered it to be primarily a defensive research facility. The US military, at the time, knew that the [[Soviet Union|USSR]] was spending 10 times more than the USA on chemical weapons development. Edgewood initially enjoyed a mandate{{Clarification needed|reason=What does "mandate" mean in this context?|date=August 2022}} and lack of oversight. Edgewood Arsenal Chemical Corps was tasked with ensuring that America was prepared with adequate counter-tactics if needed and that it could mount its own psychochemical retaliatory strike against the USSR if necessary. Edgewood performed analysis and submitted data to military commanders who could then choose to incorporate that into their strategy. In practice, however, it was mostly to make the strategists aware of special weapons and tactics that the enemy could instead deploy. The Edgewood Laboratory was originally founded in 1948. The original [[cannabinoid]] distillate (the precursor to EA-2233, called EA-1476 or "Red oil"), known today as [[THC Delta-9|delta-9-THC]], was first created in 1949, and laboratory study of EA-1476 occurred in the mid-1950s. A single batch of EA-2233 was prepared by chemist Harry Pars of A.D. Little Labs in 1962 under a top-secret government contract. It was administered to groups of consenting & informed{{Citation needed|reason=Servicemen interviewed as part of the documentary Dr. Delirium and The Edgewood Experiments refute this|date=July 2022}} enlisted servicemen by Dr. [[James S. Ketchum|James Ketchum]] in 1962. The Edgewood laboratory was shut down in 1975. Government funding for continued military development of synthetic cannabis was lacking and the cannabinoid research program was indefinitely suspended along with the rest of the Edgewood Arsenal experiments in the late 1970s for a variety of reasons. There was growing public distrust of the military and government, and there was little useful purpose for the further development of chemical incapacitating agents during and after the Vietnam era.<ref name=":0" /> Multiple newspapers criticized the EA-2233 experiments. Since the 1930s, cannabis and cannabinoids had consistently been seen by the public as dangerous and addictive drugs. DMHP was compared to BZ, a non-cannabis chemical that was cited to be useless among military planners, and was only tested once in a hastily constructed operation called "Project Dork" (part of [[Project 112]]).<ref>{{cite magazine| vauthors = Khatchadourian R | date = 12 December 2012 |title=War of the Mind|url=https://www.newyorker.com/news/news-desk/war-of-the-mind|access-date=2021-05-08|magazine=The New Yorker|language=en-US}}</ref> ==Research== === Imvestigation as non-lethal incapacitating agent === DMHP and its ''O''-[[acetate]] [[ester]] were extensively investigated by the [[United States and weapons of mass destruction#Chemical weapons|US military chemical weapons program]] in the [[Edgewood Arsenal experiments]], as possible non-lethal incapacitating agents.<ref>{{cite book| chapter-url=http://books.nap.edu/openbook.php?record_id=9136&page=79 | chapter = Possible Long-Term Health Effects of Short-Term Exposure To Chemical Agents|volume= 2 | title = Cholinesterase Reactivators, Psychochemicals and Irritants and Vesicants |year=1984|publisher= Commission on Life Sciences. The National Academies Press|pages=79–99|doi=10.17226/9136|isbn=978-0-309-07772-9}}</ref> DMHP has three [[stereocenter]]s and consequently has eight possible [[stereoisomer]]s, which differ considerably in potency. The mixture of all eight isomers of the ''O''-acetyl ester was given the code number EA-2233, with the eight individual isomers numbered EA-2233-1 through EA-2233-8. The most potent isomer is EA-2233-2, with an active dose range in humans of 0.5–2.8&nbsp;μg/kg (i.e. ~35–200&nbsp;μg for a 70&nbsp;kg adult). Active doses varied markedly between individuals, but when the dose of EA-2233 was taken up to 1–2&nbsp;mg, all volunteers were considered to be incapable of performing military duties, with the effects lasting as long as 2–3&nbsp;days. DMHP is metabolized in a similar manner to THC, producing the active metabolite 11-hydroxy-DMHP, but the [[lipophilicity]] of DMHP is even higher than that of THC itself, giving it a long duration of action and an extended half-life in the body of between 20 and 39 hours, with the half-life of the 11-hydroxy-DMHP metabolite being longer than 48 hours. DMHP and its esters produce [[sedation]] and mild [[hallucinogenic]] effects similar to large doses of [[Tetrahydrocannabinol|THC]]. However, they also cause pronounced [[hypotension]] (low blood pressure), occurring at doses well below the hallucinogenic dose, which can lead to severe [[dizziness]], [[fainting]], [[ataxia]] and [[muscle weakness]], sufficient to make it difficult to stand upright or carry out any kind of vigorous physical activity.<ref name=":0">{{cite book| vauthors = Ketchum JS |title=Chemical Warfare: Secrets Almost Forgotten|publisher=ChemBooks Inc.|year=2006|isbn=978-1-4243-0080-8 | location = Santa Rosa, CA | chapter = Chapter 5 | page = 38 }}</ref> The acute toxicity of DMHP was found to be low in both human and animal studies, with the [[therapeutic index]] measured as a ratio of [[Effective dose (pharmacology)|ED<sub>50</sub>]] to [[LD50|LD<sub>50</sub>]] in animals being around 2000 times. There have been no recorded deaths caused by any DMHP EA-2233 stereoisomers 1–8, only symptoms that are entirely consistent with the highest-known levels of THC intoxication.<ref name=":0" /> DMHP has an intravenous LD50 of 63&nbsp;mg/kg in mice and an intravenous minimal lethal dose of 10&nbsp;mg/kg in dogs.<ref>{{cite book | url=https://nap.nationalacademies.org/read/9136/chapter/5#85 | doi=10.17226/9136 | title=Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents, Volume 2 | year=1984 | isbn=978-0-309-07772-9 }}</ref> === Military application === The combination of strong incapacitating effects and a favorable safety margin led the Edgewood Arsenal team to conclude that DMHP and its derivatives, especially the O-acetyl ester of the most active isomer, EA-2233-2, were among the more promising non-lethal incapacitating agents to come out of their research program. However, DMHP had the disadvantage of sometimes producing severe [[hypotension]] at pre-incapacitating doses, which did not occur with the more widely studied and publicized belladonnoid [[anticholinergic]] agents, such as [[3-Quinuclidinyl benzilate]] (BZ), which was discovered and subsequently weaponized.<ref>{{cite book | vauthors = Ketchum JS | date = 2006 | title = Chemical Warfare Secrets Almost Forgotten | publisher = ChemBooks Inc. | isbn = 978-1-4243-0080-8}}</ref> Military applications of synthetic cannabinoids were limited because the drug was both illegal and politically toxic to study via laboratory administration to enlisted servicemen. Both EA-2233-2 and the red-oil THC distillate predecessor, EA-1476, received limited budget and resources compared to the study of other incapacitating agents of BZ derivatives and [[Lysergic acid diethylamide|LSD]], (which was widely believed at the time to be a viable mind-control and [[truth serum]] useful in a variety of Cold War applications).<ref name=":0" /> Initially, the 8 stereoisomers of EA-2233 could not be separated; later, two of the individual isomers of EA-2233 were isolated and tested, but were found to cause both [[orthostatic hypotension]] and minimal effects on performance at the very low doses used. EA-2233 did not seem to have sufficient potency to be of military interest, since an oral dose of 60mcg/kg caused a maximum decline of only 40% (at most) in performance at language and number processing tasks. == See also == * [[Tinabinol]] * [[Nabitan]] * [[Menabitan]] * [[A-40174]] * [[A-41988]] * [[Δ-3-Tetrahydrocannabinol|Δ<sup>3</sup>-Tetrahydrocannabinol]] * [[Tetrahydrocannabinol]] (THC) * [[Tetrahydrocannabiphorol]] (THCP) * [[THCP-O-acetate]] * [[Synthetic cannabinoids]] * [[Effects of cannabis]] == References == {{reflist}} {{Cannabinoids}} {{Chemical warfare}} {{Hallucinogens}} {{Cannabinoidergics}} [[Category:Benzochromenes]] [[Category:Cannabinoids]] [[Category:Incapacitating agents]] [[Category:Hydroxyarenes]] [[Category:Designer drugs]] [[Category:Analgesics]] </textarea><div class="templatesUsed"><div class="mw-templatesUsedExplanation"><p><span id="templatesused">Pages transcluded onto the current version of this page<span class="posteditwindowhelplinks"> (<a 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