{{Short description|DMAA substitute}}

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| routes_of_administration = Oral, inhaled

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| legal_US = Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in [[dietary supplement]]s, [[food]], or [[medicine]] is unlawful; otherwise uncontrolled.<ref>{{Cite web |date=March 6, 2023 |title=DMHA in Dietary Supplements |url=https://www.fda.gov/food/dietary-supplement-ingredient-directory/dmha-dietary-supplements |access-date=June 9, 2023 |website=[[FDA]]}}</ref>

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| bioavailability =

| protein_bound =

| metabolism = [[Hydroxylation]]<ref name="DibBosseTsivou2019" />

| metabolites = [[Heptaminol]]<ref name="DibBosseTsivou2019" />

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| CAS_number_Ref = {{cascite|changed|??}}

| ATC_prefix = none

| PubChem = 10982

| ChemSpiderID = 10517

| DrugBank = DB19374

| synonyms = Dimethylhexylamine; DMHA; Ottodrina; Vaporpac; Amidrine; 2-Aminoisooctane; 2-Amino-6-methylheptane; 1,5-Dimethylhexylamine; 6-Methyl-2-heptylamine; 6-Methyl-2-heptanamine; Isoctaminium; SKF-51; SK&F-51; NSC-759813<ref>

{{PubChem|10982}}</ref>

| C=8 | H=19 | N=1

| SMILES = CC(C)CCCC(C)N

| StdInChI = 1S/C8H19N/c1-7(2)5-4-6-8(3)9/h7-8H,4-6,9H2,1-3H3

| StdInChIKey = QNIVIMYXGGFTAK-UHFFFAOYSA-N

'''Octodrine''', also known as '''dimethylhexylamine''' ('''DMHA''') and sold under the brand name '''Vaporpac''' among others, is a [[sympathomimetic]] and [[stimulant]] [[medication]] that was formerly used in the treatment of [[hypotension]] (low blood pressure).<ref name="MortonHall2012" /><ref name="CatalaniPrilutskayaAl-Imam2018">{{cite journal | vauthors = Catalani V, Prilutskaya M, Al-Imam A, Marrinan S, Elgharably Y, Zloh M, Martinotti G, Chilcott R, Corazza O | title = Octodrine: New Questions and Challenges in Sport Supplements | journal = Brain Sci | volume = 8 | issue = 2 | date = February 2018 | page = 34 | pmid = 29461475 | pmc = 5836053 | doi = 10.3390/brainsci8020034 | doi-access = free | url = }}</ref>

It has been studied in a dozen [[animal study|animal studies]] from the 1940s through the 1970s. These studies found that octodrine can increase [[blood pressure]] and [[cardiac output]] in animals. The drug was previously approved for use by the [[Food and Drug Administration]] (FDA) as an [[inhalant]] (i.e., ''Vaporpac'' and ''Tickle Tackle Inhaler'') and in [[Germany]] as an [[oral administration|oral]] [[medication]] as part of a [[combination drug|multi-component]] medication (i.e., ''Ambredin'' and ''Ordinal''), but is no longer available.<ref name="Clin Tox">{{cite journal | vauthors = Cohen PA, Travis JC, Keizers PH, Deuster P, Venhuis BJ | s2cid = 5193271 | title = Four experimental stimulants found in sports and weight loss supplements: 2-amino-6-methylheptane (octodrine), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylamylamine (1,3-DMAA) and 1,3-dimethylbutylamine (1,3-DMBA) | journal = Clinical Toxicology | volume = 56 | issue = 6 | pages = 421–426 | date = June 2018 | pmid = 29115866 | doi = 10.1080/15563650.2017.1398328 }}</ref>

DMHA has also been found as an [[adulterant]] in sports supplements and is sold online as a [[designer drug]].<ref name="Clin Tox"/><ref>{{Cite web|url=https://www.usada.org/spirit-of-sport/education/designer-stimulants-what-athletes-should-know/|title=Designer Stimulants: What Athletes Should Know &#124; USADA|date=24 January 2019 }}</ref> The presence of a reductive amination byproduct confirms its synthetic origin.<ref name=" J. Pharm. Biomed. Anal.">{{cite journal | vauthors = Wang M, Haider S, Chittiboyina AG, Parcher JF, Khan IA| s2cid = 5193271 | title = 1,5-Dimethylhexylamine (octodrine) in sports and weight loss supplements: Natural constituent or synthetic chemical? | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 152 | pages = 298–305 | date = April 2018 | pmid = 29454882 | doi = 10.1016/j.jpba.2018.02.008 }}</ref>

In the United States, the FDA considers DMHA to be an unsafe ingredient in [[dietary supplement]]s.<ref name="fda-23">{{cite web |title=DMHA in Dietary Supplements |url=https://www.fda.gov/food/information-select-dietary-supplement-ingredients-and-other-substances/dmha-dietary-supplements |publisher=US Food and Drug Administration |access-date=14 September 2024 |date=6 March 2023}}</ref>

In 2019, the FDA issued nine [[FDA warning letter|warning letters]] to US manufacturers of dietary supplements containing DMHA as an unsafe food additive, deeming such products to be adulterated and illegal for marketing.<ref name="fda-19">{{cite web |title=FDA Acts on Dietary Supplements Containing DMHA and Phenibut |url=https://www.fda.gov/food/cfsan-constituent-updates/fda-acts-dietary-supplements-containing-dmha-and-phenibut |publisher=US Food and Drug Administration |access-date=14 September 2024 |date=29 April 2019}}</ref>

==Side effects==

Reported [[side effect]]s of octodrine include [[hypertension]], [[dyspnea]], and [[hyperthermia]].<ref name="CatalaniPrilutskayaAl-Imam2018" />

==Pharmacology==

It is described as a [[sympathomimetic]], [[vasoconstrictor]], and [[local anesthetic]].<ref name="CatalaniPrilutskayaAl-Imam2018" /><ref name="Elks2014" />

===Pharmacokinetics===

[[Heptaminol]] is an [[active metabolite]] of octodrine.<ref name="DibBosseTsivou2019">{{cite journal | vauthors = Dib J, Bosse C, Tsivou M, Glatt AM, Geisendorfer T, Geyer H, Gmeiner G, Sigmund G, Thevis M | title = Is heptaminol a (major) metabolite of octodrine? | journal = Drug Test Anal | volume = 11 | issue = 11–12 | pages = 1761–1763 | date = November 2019 | pmid = 31763761 | doi = 10.1002/dta.2737 | url = | doi-access = free }}</ref>

==Chemistry==

===Related compounds===

* [[Isometheptene]]

* [[Methylhexanamine]] (DMAA)

* [[Tuaminoheptane]]

* [[1,3-Dimethylbutylamine]] (DMBA)

* [[Iproheptine]] (''N''-isopropyloctodrine)

* [[Heptaminol]] (hydroxyoctodrine)

==Society and culture==

===Names===

Octodrine is the [[generic term|generic name]] of the drug and its {{Abbrlink|INN|International Nonproprietary Name}} and {{Abbrlink|USAN|United States Adopted Name}}.<ref name="Elks2014">{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA802 | access-date=30 August 2024 | page=802}}</ref><ref name="MortonHall2012">{{cite book | vauthors = Morton IK, Hall JM | title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms | publisher=Springer Netherlands | year=2012 | isbn=978-94-011-4439-1 | url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA206 | access-date=30 August 2024 | page=206}}</ref> It is also known by its former developmental code name ''SKF-51''.<ref name="Elks2014" />

===As an unsafe dietary ingredient===

In the United States, DMHA is not eligible for use as a dietary ingredient, is not approved for use in manufactured foods or dietary supplements, and is not considered to be safe for human consumption (is not [[Generally recognized as safe|GRAS]]); in regarding DMHA as an unsafe food additive, the FDA has warned manufacturers that dietary supplements containing DMHA are adulterated and illegal for marketing.<ref name=fda-23/><ref name=fda-19/>

{{Monoamine releasing agents}}

[[Category:Abandoned drugs]]

[[Category:Alkylamines]]

[[Category:Antihypotensive agents]]

[[Category:Drugs acting on the nervous system]]

[[Category:Drugs in sport]]

[[Category:Ergogenic aids]]

[[Category:Local anesthetics]]

[[Category:Stimulants]]

[[Category:Sympathomimetics]]

[[Category:Vasoconstrictors]]

[[Category:World Anti-Doping Agency prohibited substances]]