Octodrine

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).^[4][5]

Octodrine

Clinical data
Other names	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[1]
Routes of administration	Oral, inhaled
ATC code	none
Legal status
Legal status	US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.[2]
Pharmacokinetic data
Metabolism	Hydroxylation[3]
Metabolites	Heptaminol[3]
Identifiers
IUPAC name 6-methylheptan-2-amine
CAS Number	543-82-8 N
PubChem CID	10982
DrugBank	DB19374
ChemSpider	10517
UNII	3GQ9E911BI
CompTox Dashboard (EPA)	DTXSID8046535
ECHA InfoCard	100.008.047
Chemical and physical data
Formula	C8H19N
Molar mass	129.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)CCCC(C)N
InChI InChI=1S/C8H19N/c1-7(2)5-4-6-8(3)9/h7-8H,4-6,9H2,1-3H3 Key:QNIVIMYXGGFTAK-UHFFFAOYSA-N
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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.^[6]

DMHA has also been found as an adulterant in sports supplements and is sold online as a designer 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 in dietary supplements.^[9] 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.^[10]

Side effects

Reported side effects of octodrine include hypertension, dyspnea, and hyperthermia.^[5]

Pharmacology

It is described as a sympathomimetic, vasoconstrictor, and local anesthetic.^[5][11]

Pharmacokinetics

Heptaminol is an active metabolite of octodrine.^[3]

Chemistry

Related compounds

• Isometheptene
• Methylhexanamine (DMAA)
• Tuaminoheptane
• 1,3-Dimethylbutylamine (DMBA)
• Iproheptine (N-isopropyloctodrine)
• Heptaminol (hydroxyoctodrine)

Society and culture

Names

Octodrine is the generic name of the drug and its INNTooltip International Nonproprietary Name and USANTooltip United States Adopted Name.^[11][4] It is also known by its former developmental code name SKF-51.^[11]

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 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.^[9][10]

References

1. CID 10982 from PubChem
2. "DMHA in Dietary Supplements". FDA. March 6, 2023. Retrieved June 9, 2023.
3. Dib 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. Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 206. ISBN 978-94-011-4439-1. Retrieved 30 August 2024.
5. Catalani 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. Cohen 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. "DMHA in Dietary Supplements". US Food and Drug Administration. 6 March 2023. Retrieved 14 September 2024.
10. "FDA Acts on Dietary Supplements Containing DMHA and Phenibut". US Food and Drug Administration. 29 April 2019. Retrieved 14 September 2024.
11. Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 802. ISBN 978-1-4757-2085-3. Retrieved 30 August 2024.