Octopamine (drug)

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For octopamine as an invertebrate neurotransmitter, see Octopamine (neurotransmitter).
Octopamine
Octopamin.svg
Ball-and-stick model of the octopamine molecule
Systematic (IUPAC) name
(RS)-4-(2-amino-1-hydroxy-ethyl)phenol
Clinical data
Legal status
Routes of
administration
Oral
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 104-14-3 YesY
ATC code C01CA18 (WHO)
PubChem CID: 4581
IUPHAR/BPS 2149
ChemSpider 4420 YesY
UNII 14O50WS8JD YesY
ChEBI CHEBI:17134 N
ChEMBL CHEMBL53929 YesY
Synonyms Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, para-hydroxy-phenyl-ethanolamine
Chemical data
Formula C8H11NO2
Molecular mass 153.178 g/mol
 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

  1. 1.0 1.1 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. 
  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.