Myristicin

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Structural formula
Structural formula of myristicin
General
Surname Myristicin
other names
  • 5-allyl-1-methoxy-2,3- (methylenedioxy) benzene
  • 5-allyl-2,3- (methylenedioxy) anisole
  • 6-allyl-4-methoxy-1,3-benzodioxole
  • 4-methoxy-6-prop-2-enyl-1,3-benzodioxole
Molecular formula C 11 H 12 O 3
Brief description

Oil smelling of nutmeg

External identifiers / databases
CAS number 607-91-0
EC number 210-146-9
ECHA InfoCard 100.009.225
PubChem 4276
ChemSpider 4125
Wikidata Q414057
properties
Molar mass 192.2 g mol −1
Physical state

liquid

density

1.1416 (20  ° C )

Melting point

−20 ° C

boiling point

276.5 ° C

solubility
Refractive index

1.5403 (20 ° C)

safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 361f-412
P: 201-273-308 + 313
Toxicological data

4260 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Myristicin is a phenylpropanoid and an essential ingredient in nutmeg essential oil . It belongs to the group of MAO inhibitors .

Occurrence

Nutmeg contains myristicin.

Myristicin is part of the essential oil of some aromatic plants. It is contained in nutmeg ( Myristica fragrans ) and in many umbellifers , for example in dill ( Anethum graveolens ), lovage ( Levisticum officinale ), parsnips ( Pastinaca sp.) And parsley ( Petroselinum crispum ). In the essential oil of the Australian red family Zieria , the proportion is up to 23.4%.

Structurally related ones are safrole , elemicin and apiol .

use

Nutmeg used to be used for abortion when ground in beer. In Indonesia, the home of the nutmeg trees, a sedative was also made from the essential oil of nutmeg.

It was also used as an insecticide and disinfectant in the past due to its toxic effects on microorganisms.

Pharmacological properties

Myristicin is hallucinogenic . The psychotropic effect is due to its nature as a weak monoamine oxidase inhibitor .

Myristicin, like many other phenylpropanes with a terminal methylenedioxy group, can damage DNA. It is therefore considered carcinogenic and genotoxic. Since this also happens in the zygote, it has an abortion effect.

Legal status

While mescaline and MDMA are banned, nutmeg is available over the counter. The strongly psychoactive, myristicin-containing oil is in a legal gray area.

Individual evidence

  1. ↑ a b Entry on Safrol. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
  2. ↑ a b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-382.
  3. ↑ a b c d Entry on myristicin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ a b Myristicin data sheet at Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
  5. ^ Peter Nuhn: Naturstoffchemie , S. Hirzel Wissenschaftliche Verlagsgesellschaft Stuttgart, 1990, p. 528, ISBN 3-7776-0473-9 .
  6. ↑ a b Alexander Shulgin: Possible implication of myristicin as a psychotropic substance . In: Nature . No. 210 , 1966, pp. 380-384 .
  7. ↑ a b c Christian Rätsch: Encyclopedia of psychoactive plants . Aarau 2007.
  8. ↑ a b Michael Wink, Coralie Wink, Ben-Erik van Wyk: Handbook of poisonous and psychoactive plants . Stuttgart 2008.
  9. ↑ Stein, Hentschel: Nutmeg (myristicin) poisoning - report on a fatal case and a series of cases reported by a poison information center . In: Forensic science international . No. 118 , 2001, p. 87-90 .

literature

Web links