IUPAC name 4-(2-dimethylaminoethyl)phenol
Other names N,N-Dimethyltyramine
CAS number [3595-05-9]
Molecular formula C10H15NO
Molar mass 165.23 g mol-1
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
Hordenine (N,N-dimethyltyramine) is a phenylethylamine alkaloid which stimulates the release of norepinephrine in higher animals.
Occurrence in nature
Peyote (Lophophora williamsii), San Pedro cactus (Echinopsis pachanoi), and Peruvian Torch cactus (Echinopsis peruviana) all produce high levels of this compound. These cacti also produce high levels of mescaline and other phenylethylamine compounds.
Cacti in the genus Ariocarpus, Opuntia, Pereskia, and Coryphantha also produce these alkaloids, though not in high concentrations.
Aztekium also contains it.
Hordenine is an ingredient of some plants used as feed for animals, such as sprouted barley and certain grasses. Hordenine is an indirectly acting adrenergic substance available without a prescription. Hordenine is known as N,N-dimethyltyramine.
Hordenine supplement use
Hordenine has been promoted as a weight loss agent with the claim that it stimulates the central nervous system.
Phenylalkylamine alkaloids from Stapelia hirsuta L.
Nat Prod Res. 2006 Jul 10;20(8):710-4. Department of Pharmacognosy, College of Pharmacy, Cairo University, Cairo, Egypt.
Four alkaloids of the phenethylamine derivatives have been isolated from the n-butanol fraction of the aerial parts of Stapelia hirsuta L. The structures of the isolated alkaloids were determined as N-acetyl hordenine (a new natural compound), hordenine, candicine and hordenine -1-O-beta-D-glucoside, in addition to luteolin-7-O-beta-D-glucopyranoside.
Pharmacological effects of hordenine
Dtsch Tierarztl Wochenschr. 1995 Jun;102(6):228-32. Institut fur Pharmakologie, Toxikologie und Pharmazie, Tierarztlichen Hochschule Hannover.
After ingestion of plants with hordenine may be detected in blood or urine of horses. Hordenine liberates norepinephrine from stores. In isolated organs and those structures with reduced epinephrine contents the hordenine effect is only very poor. Experiments in intact animals (rats, dogs) show that hordenine has a positive inotropic effect upon the heart, increases systolic and diastolic blood pressure, peripheral blood flow volume, inhibits gut movements but has no effect upon the psychomotorical behaviour of mice. All effects are short and only possible after high doses which are not to be expected after ingestion of hordenine containing feed for horses. A measurable increase of the performance of racing horses is quite improbable.
Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse.
Equine Vet J. 1990 Nov;22(6):437-41. Kentucky Equine Drug Research Program, Graduate Center in Toxicology, University of Kentucky, Lexington
We investigated the pharmacological actions of hordenine in the horse. Hordenine (2.0 mg/kg bodyweight [bwt]) was administered by rapid intravenous (iv) injection to 10 horses. Typically, dosed horses showed a flehmen response and defecated within 60 seconds. All horses showed substantial respiratory distress. Respiratory rates increased about 250 per cent and heart rates were approximately double that of resting values. All animals broke out in a sweat shortly after iv injection, but basal body temperature was not affected. These effects were transient, and the animals appeared normal within 30 minuntes of dosing. Treated horses were tested in a variable interval responding apparatus 30 mins after dosing and no residual stimulation or depressant effects of hordenine were apparent. Animals dosed orally with 2.0 mg/kg bwt of hordenine showed no changes in heart rate, respiratory rate, basal body temperature or behaviour. After iv injection of hordenine, (2.0 mg/kg bwt) plasma reached a maximum value of about 1.0 micrograms/ml, and declined thereafter in a biexponential fashion.
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