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Octodrine

From Wikipedia, the free encyclopedia
DMAA substitute

Pharmaceutical compound
Octodrine
Clinical data
Other namesDimethylhexylamine; DMHA; Ottodrina; Vaporpac; Amidrine; 2-Aminoisooctane;2-aminoisoheptane; 2-Amino-6-methylheptane; 1,5-Dimethylhexylamine; 6-Methyl-2-heptylamine; 6-Methyl-2-heptanamine; Isoctaminium; SKF-51; SK&F-51; NSC-759813[1]
Routes of
administration
Oral, inhaled
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
MetabolismHydroxylation[3]
MetabolitesHeptaminol[3]
Identifiers
  • 6-methylheptan-2-amine
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.008.047Edit this at Wikidata
Chemical and physical data
FormulaC8H19N
Molar mass129.247 g·mol−1
3D model (JSmol)
  • CC(C)CCCC(C)N
  • InChI=1S/C8H19N/c1-7(2)5-4-6-8(3)9/h7-8H,4-6,9H2,1-3H3
  • Key:QNIVIMYXGGFTAK-UHFFFAOYSA-N
  (verify)

Octodrine, also known asdimethylhexylamine (DMHA) and sold under the brand nameVaporpac among others, is asympathomimetic andstimulantmedication that was formerly used in the treatment ofhypotension (low blood pressure).[4][5]

It has been studied in a dozenanimal studies from the 1940s through the 1970s. These studies found that octodrine can increaseblood pressure andcardiac output in animals. The drug was previously approved for use by theFood and Drug Administration (FDA) as aninhalant (i.e.,Vaporpac andTickle Tackle Inhaler) and inGermany as anoralmedication as part of amulti-component medication (i.e.,Ambredin andOrdinal), but is no longer available.[6]

DMHA has also been found as anadulterant in sports supplements and is sold online as adesigner drug.[6][7] The presence of a reductive amination byproduct confirms its synthetic origin.[8]

In the United States, the FDA considers DMHA to be an unsafe ingredient indietary supplements.[9]In 2019, the FDA issued ninewarning letters to US manufacturers of dietary supplements containing DMHA as an unsafe food additive, deeming such products to be adulterated and illegal for marketing.[10]

Side effects

[edit]

Reportedside effects of octodrine includehypertension,dyspnea, andhyperthermia.[5]

Pharmacology

[edit]

It is described as asympathomimetic,vasoconstrictor, andlocal anesthetic.[5][11]

Pharmacokinetics

[edit]

Heptaminol is anactive metabolite of octodrine.[3]

Chemistry

[edit]

Related compounds

[edit]

Society and culture

[edit]

Names

[edit]

Octodrine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name andUSANTooltip United States Adopted Name.[11][4] It is also known by its former developmental code nameSKF-51.[11]

As an unsafe dietary ingredient

[edit]

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 notGRAS); in regarding DMHA as an unsafe food additive, the FDA has warned manufacturers that dietary supplements containing DMHA are adulterated and illegal for marketing.[9][10]

References

[edit]
  1. ^CID 10982 fromPubChem
  2. ^"DMHA in Dietary Supplements".FDA. March 6, 2023. RetrievedJune 9, 2023.[dead link]
  3. ^abcDib J, Bosse C, Tsivou M, Glatt AM, Geisendorfer T, Geyer H, et al. (November 2019)."Is heptaminol a (major) metabolite of octodrine?".Drug Test Anal.11 (11–12):1761–1763.doi:10.1002/dta.2737.PMID 31763761.
  4. ^abMorton IK, Hall JM (2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 206.ISBN 978-94-011-4439-1. Retrieved30 August 2024.
  5. ^abcCatalani V, Prilutskaya M, Al-Imam A, Marrinan S, Elgharably Y, Zloh M, et al. (February 2018)."Octodrine: New Questions and Challenges in Sport Supplements".Brain Sci.8 (2): 34.doi:10.3390/brainsci8020034.PMC 5836053.PMID 29461475.
  6. ^abCohen PA, Travis JC, Keizers PH, Deuster P, Venhuis BJ (June 2018). "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)".Clinical Toxicology.56 (6):421–426.doi:10.1080/15563650.2017.1398328.PMID 29115866.S2CID 5193271.
  7. ^"Designer Stimulants: What Athletes Should Know | USADA". 24 January 2019.
  8. ^Wang M, Haider S, Chittiboyina AG, Parcher JF, Khan IA (April 2018)."1,5-Dimethylhexylamine (octodrine) in sports and weight loss supplements: Natural constituent or synthetic chemical?".Journal of Pharmaceutical and Biomedical Analysis.152:298–305.doi:10.1016/j.jpba.2018.02.008.PMID 29454882.S2CID 5193271.
  9. ^ab"DMHA in Dietary Supplements". US Food and Drug Administration. 6 March 2023. Retrieved14 September 2024.
  10. ^ab"FDA Acts on Dietary Supplements Containing DMHA and Phenibut". US Food and Drug Administration. 29 April 2019. Archived fromthe original on July 25, 2019. Retrieved14 September 2024.
  11. ^abcElks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 802.ISBN 978-1-4757-2085-3. Retrieved30 August 2024.
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