octodrine

{{Short description|DMAA substitute}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| verifiedrevid = 449583899

| IUPAC_name = 6-methylheptan-2-amine

| image = Octodrine.png

| width = 180px

| tradename =

| dependency_liability =

| addiction_liability =

| routes_of_administration = Oral, inhaled

| legal_US = Unapproved drug; use in dietary supplements, food, or medicine is unlawful.{{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}}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}

| legal_status =

| bioavailability =

| protein_bound =

| metabolism = Hydroxylation

| metabolites = Heptaminol

| onset =

| elimination_half-life =

| duration_of_action =

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

| CAS_number = 543-82-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3GQ9E911BI

| 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

{{PubChem|10982}}

| 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).{{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 = }}

It has been studied in a dozen 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 medication as part of a multi-component medication (i.e., Ambredin and Ordinal), but is no longer available.{{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 }}

DMHA has also been found as an adulterant in sports supplements and is sold online as a designer drug.{{Cite web|url=https://www.usada.org/spirit-of-sport/education/designer-stimulants-what-athletes-should-know/|title=Designer Stimulants: What Athletes Should Know | USADA|date=24 January 2019 }} The presence of a reductive amination byproduct confirms its synthetic origin.{{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 | doi-access = free }}

In the United States, the FDA considers DMHA to be an unsafe ingredient in dietary supplements.{{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}}

In 2019, the FDA issued nine 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.{{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 |archive-url=https://web.archive.org/web/20190725143327/https://www.fda.gov/food/cfsan-constituent-updates/fda-acts-dietary-supplements-containing-dmha-and-phenibut |url-status=dead |archive-date=July 25, 2019 |publisher=US Food and Drug Administration |access-date=14 September 2024 |date=29 April 2019}}