Octopamine

Overview

Octopamine (OA), also known as para-octopamine and norsynephrine among synonyms, is an organic chemical closely related to norepinephrine, and synthesized biologically by a homologous pathway. Octopamine is often considered the major "fight-or-flight" neurohormone of invertebrates. Its name is derived from the fact that it was first identified in the salivary glands of the octopus. WP

In many types of invertebrates, octopamine is an important neurotransmitter and hormone. In protostomes—arthropods, molluscs, and several types of worms—it substitutes for norepinephrine and performs functions apparently similar to those of norepinephrine in mammals, functions that have been described as mobilizing the body and nervous system for action. In mammals, octopamine is found only in trace amounts (i.e., it is a trace amine), and no biological function has been solidly established for it. It is also found naturally in numerous plants, including bitter orange.[1][2] WP

Octopamine has been sold under trade names such as Epirenor, Norden, and Norfen for use as a sympathomimetic drug, available by prescription. WP

Pharmacology

Pharmacology

Octopamine has been sold under trade names such as Epirenor, Norden, and Norfen for use in medicine as a sympathomimetic drug, available by prescription. However, very little information exists concerning its clinical usefulness or safety. It has been studied as an antihypotensive agent and has been shown to increase blood pressure when administered intravenously, intramuscularly, and buccally at sufficiently high doses, whereas oral administration was ineffective.[3] WP

Octopamine is an analogue of sympathomimetic catecholamines like norepinephrine and phenethylamines like tyramine. However, octopamine has 400- to 2,000-fold lower affinity for the mammalian α- and β-adrenergic receptors than norepinephrine. In any case, it can produce significant sympathomimetic effects, like pressor responses, at sufficiently high doses.[3] WP

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] WP

The World Anti-Doping Agency lists octopamine as a banned substance for in competition use, as a "specified stimulant" on the 2019 Prohibited List.[5] WP⚠ A word may be missing here. It reads this way in the source too.

In contrast to various other phenethylamines, octopamine is a poor or negligible substrate of the dopamine transporter (DAT).[6][7][8] WP

Chemistry

Formula

C8H11NO2 PC

CAS number

104-14-3 PC

Molar mass (g/mol)

153.18 PC

IUPAC name (computed by PubChem)

4-(2-amino-1-hydroxyethyl)phenol PC

SMILES

C1=CC(=CC=C1C(CN)O)O PC

InChIKey

QHGUCRYDKWKLMG-UHFFFAOYSA-N PC

PubChem CID

4581

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Tang F, Tao L, Luo X, Ding L, Guo M, Nie L, Yao S. Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography. Journal of Chromatography A. September 2006. doi:10.1016/j.chroma.2006.05.049 · PMID 16781718
2. Journal / agency Jagiełło-Wójtowicz E. Mechanism of central action of octopamine. Polish Journal of Pharmacology and Pharmacy. 1979. PMID 121158
3. Journal / agency Stohs SJ. Physiological functions and pharmacological and toxicological effects of p-octopamine. Drug and Chemical Toxicology. January 2015. doi:10.3109/01480545.2014.900069 · PMID 24654910
4. Journal / agency Haller CA, Benowitz NL, Jacob P. Hemodynamic effects of ephedra-free weight-loss supplements in humans. The American Journal of Medicine. September 2005. doi:10.1016/j.amjmed.2005.02.034 · PMID 16164886
5. Other Prohibited In Competition – Stimulants
6. Journal / agency Liu J, Wu R, Li JX. TAAR1 and Psychostimulant Addiction. Cell Mol Neurobiol. March 2020. doi:10.1007/s10571-020-00792-8 · PMID 31974906 · PMC7845786
7. Journal / agency Underhill SM, Hullihen PD, Chen J, Fenollar-Ferrer C, Rizzo MA, Ingram SL, Amara SG. Amphetamines signal through intracellular TAAR1 receptors coupled to Gα13 and GαS in discrete subcellular domains. Mol Psychiatry. April 2021. doi:10.1038/s41380-019-0469-2 · PMID 31399635 · PMC7038576
8. Journal / agency Pörzgen P, Park SK, Hirsh J, Sonders MS, Amara SG. The antidepressant-sensitive dopamine transporter in Drosophila melanogaster: a primordial carrier for catecholamines. Mol Pharmacol. January 2001. doi:10.1124/mol.59.1.83 · PMID 11125028

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.