Octopamine (drug)

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Octopamine
Octopamin.svg
Ball-and-stick model of the octopamine molecule
Clinical data
Synonyms Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, para-hydroxy-phenyl-ethanolamine
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 99.42 %
Metabolism p-hydroxymandelic acid (if p-octopamine) or m-hydroxymandelic acid (if m-octopamine[1][2]
Biological half-life 15 minutes in insects. Between 76 and 175 minutes in humans
Excretion Up to 93% of ingested octopamine is eliminated via the urinary route within 24 hours[1]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
Formula C8H11NO2
Molar mass 153.178 g/mol
3D model (JSmol)
Chirality Racemic mixture
 NYesY (what is this?)  (verify)

Octopamine (molecular formula C8H11NO2) is an organic chemical closely related to norepinephrine. In many types of invertebrates it functions as an important neurotransmitter and hormone, but in the human body it normally exists only at trace levels and has no known function. Because it shares some of the actions of norepinephrine, octopamine has been sold under trade names such as Epirenor, Norden, and Norfen for use as a sympathomimetic drug, available by prescription. Very little information exists concerning its clinical usefulness or safety.[3]

In mammals, octopamine may mobilize the release of fat from adipocytes (fat cells), which has led to its promotion on the internet as a slimming aid. However, the released fat is likely to be promptly taken up into other cells, and there is no evidence that octopamine facilitates weight loss. Octopamine may also increase blood pressure significantly when combined with other stimulants, as in some weight loss supplements.[4]

References[edit]

  1. ^ a b Hengstmann, J. H.; Konen, W; Konen, C; Eichelbaum, M; Dengler, H. J. (1974). "The physiological disposition of p-octopamine in man". Naunyn-Schmiedeberg's Archives of Pharmacology. 283 (1): 93–106. PMID 4277715. doi:10.1007/bf00500148. 
  2. ^ d’Andrea, Giovanni; Nordera, Gianpietro; Pizzolato, Gilberto; Bolner, Andrea; Colavito, Davide; Flaibani, Raffaella; Leon, Alberta (2010). "Trace amine metabolism in Parkinson's disease: Low circulating levels of octopamine in early disease stages". Neuroscience Letters. 469 (3): 348–51. PMID 20026245. doi:10.1016/j.neulet.2009.12.025. 
  3. ^ Stohs SJ (2015). "Physiological functions and pharmacological and toxicological effects of p-octopamine". Drug Chem Toxicol. 38 (1): 106–12. PMID 24654910. doi:10.3109/01480545.2014.900069. 
  4. ^ Haller, Christine A.; Benowitz, Neal L.; Jacob, Peyton (2005). "Hemodynamic effects of ephedra-free weight-loss supplements in humans". The American Journal of Medicine. 118 (9): 998–1003. PMID 16164886. doi:10.1016/j.amjmed.2005.02.034.