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Myristicin information


Myristicin
Clinical data
Other names3-methoxy-4,5-methylenedioxy-allylbenzene; 5-methoxy-3,4-methylenedioxy-allylbenzene
Dependence
liability
Unknown
Addiction
liability
Low
Routes of
administration
Oral
Legal status
Legal status
  • In general: uncontrolled, could be illegal in the UK under the Psychoactive Substances Act 2016 if it's sold for human consumption or synthetized for recreational use.
Identifiers
IUPAC name
  • 7-Allyl-5-methoxy-1,3-benzodioxole
CAS Number
  • 607-91-0 checkY
PubChem CID
  • 4276
ChemSpider
  • 4125 checkY
UNII
  • 04PD6CT78W
KEGG
  • C10480 checkY
ChEMBL
  • ChEMBL481044 checkY
CompTox Dashboard (EPA)
  • DTXSID1025693 Edit this at Wikidata
ECHA InfoCard100.009.225 Edit this at Wikidata
Chemical and physical data
FormulaC11H12O3
Molar mass192.214 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O1c2cc(cc(OC)c2OC1)C\C=C
InChI
  • InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3 checkY
  • Key:BNWJOHGLIBDBOB-UHFFFAOYSA-N checkY
  (verify)

Myristicin is a naturally occurring compound found in common herbs and spices, such as nutmeg.[1][2] It is an insecticide, and has been shown to enhance the effectiveness of other insecticides.[1][3]

When ingested, myristicin may produce hallucinogenic effects,[1][4] and can be converted to MMDMA in controlled chemical synthesis.[5] It interacts with many enzymes and signaling pathways in the body,[6][7] and may have dose-dependent cytotoxicity in living cells.[6] Myristicin is listed in the Hazardous Substances Data Bank.[1]

  1. ^ a b c d "Myristicin". PubChem, US National Library of Medicine. 13 May 2023. Retrieved 14 May 2023.
  2. ^ "Nutmeg". Drugs.com. 21 November 2022. Retrieved 14 May 2023.
  3. ^ Lichtenstein EP, Casida JE (1963). "Naturally Occurring Insecticides, Myristicin, an Insecticide and Synergist Occurring Naturally in the Edible Parts of Parsnips". Journal of Agricultural and Food Chemistry. 11 (5): 410–415. doi:10.1021/jf60129a017.
  4. ^ Stein U, Greyer H, Hentschel H (April 2001). "Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre". Forensic Science International. 118 (1): 87–90. doi:10.1016/s0379-0738(00)00369-8. PMID 11343860.
  5. ^ Clark CR, DeRuiter J, Noggle FT (1996-01-01). "Analysis of 1-(3-Methoxy-4,5-Methylenedioxyphenyl)-2-Propanamine(MMDA)Derivatives Synthesized from Nutmeg Oil and 3-Methoxy-4,5-Methylenedioxybenzaldehyde". Journal of Chromatographic Science. 34 (1): 34–42. doi:10.1093/chromsci/34.1.34.
  6. ^ a b Lee BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, et al. (May 2005). "Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells". Toxicology Letters. 157 (1): 49–56. doi:10.1016/j.toxlet.2005.01.012. PMID 15795093.
  7. ^ Yang AH, He X, Chen JX, He LN, Jin CH, Wang LL, et al. (July 2015). "Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2". Chemico-Biological Interactions. 237: 133–40. doi:10.1016/j.cbi.2015.06.018. PMID 26091900.

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Myristicin

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Myristicin is a naturally occurring compound found in common herbs and spices, such as nutmeg. It is an insecticide, and has been shown to enhance the...

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Nutmeg

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safrol, and myristicin. In its pure form, myristicin is a toxin, and consumption of excessive amounts of nutmeg can result in myristicin poisoning. The...

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Dill

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was transformed into the plant. Apiole and dillapiole Carvone Limonene Myristicin Umbelliferone Fresh and dried dill leaves (sometimes called "dill weed"...

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PiHKAL

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ten amphetamines that differ from natural products such as safrole or myristicin by an amine group (PIHKAL Entry #157 TMA). The list consists of: PMA...

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Magnoliids

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exuded from the bark of Virola trees. Another hallucinogenic compound, myristicin, comes from the spice nutmeg. As with safrole, ingestion of nutmeg in...

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Parsley

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hearts providing 19.1 mg/100 grams. Parsley essential oil is high in myristicin. Excessive consumption of parsley should be avoided by pregnant women...

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Elemicin

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oils respectively. Structurally, elemicin is similar to myristicin, differing only by myristicin's methyl group that joins the two oxygen atoms that make...

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Eugenol

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withdrawn) and the widely used propofol. Eugenol and the structurally similar myristicin, have the common property of inhibiting MAO-A and MAO-B in vitro. In humans...

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Insecticide

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Eugenol (mosquito larvae) Hinokitiol Ivermectin Limonene Linalool Menthol Myristicin Neem (Azadirachtin) Nicotine Nootkatone Peganum harmala, seeds (smoke...

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Piper guineense

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agent. It also contains significant proportions (up to around 10%) of myristicin, elemicin, safrole, and dillapiol, as well as some apiole (around 1.4%)...

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Deliriant

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anticholinergic-like symptoms when taken in large doses. The effects caused by myristicin and elemicin found in nutmeg's essential oil can last up to several days...

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Nutmeg oil

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small amounts of various phenolic compounds and aromatic ethers, e.g. myristicin, elemicin, safrole, and methyl eugenol. The phenolic fraction is considered...

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Apiole

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and Crowea angustifolia var. angustifolia.[citation needed] Dillapiole Myristicin Azeez, Shamina; Krishnamurthy, K. (2008). Chemistry of Spices. Calicut...

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Recreational drug use

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in the Solanaceae) hyoscine hydrobromide (another Solanaceae alkaloid) myristicin (found in Myristica fragrans ("Nutmeg")) ibotenic acid (found in Amanita...

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Oneirogen

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agonists like Zolpidem[citation needed] Nutmeg in commonly used amounts myristicin and elemicin, can increase vividness of dreams[citation needed] Water...

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List of poisonous plants

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BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, Ko KH, Ryu JH (2005). "Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells". Toxicol....

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Myristicaceae

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some genera, such as Virola, contains several hallucinogenic alkaloids. Myristicin poisoning can induce convulsions, palpitations, nausea, eventual dehydration...

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Synthetic cannabinoids

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reversible monoamine oxidase inhibitors, which have been found with myristicin and asarone; substituted cathinone derived stimulant drugs such as 4-methylbuphedrone...

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Phenylpropanoid

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Asarone Chavicol Dillapiole Elemicin Estragole Eugenol Methyl eugenol Myristicin Eleutherosides Barros J, Serrani-Yarce JC, Chen F, Baxter D, Venables...

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Piper excelsum

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grown as an ornamental plant in gardens. Kawakawa essential oil contains myristicin, a deliriant when consumed in high concentrations. Kawakawa is sometimes...

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Glossary of chemical formulae

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3-indolepropionic acid 830-96-6 C11H12N2O2 tryptophan Trp 73-22-3 C11H12O3 myristicin C11H13NO6 Caramboxin or Diroximel fumarate C11H14N2O 5-methoxytryptamine...

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Falcarinol

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R. E. England (1982). "Isolation and analysis of carrot constituents: myristicin, falcarinol, and falcarindiol". Journal of Agricultural and Food Chemistry...

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Alexander Shulgin

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related to mescaline". Experientia 19: 127. 19 1963. "Composition of the myristicin fraction from oil of nutmeg". Nature 197: 379. 20 1963. "Concerning the...

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C11H12O3

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21 g/mol) may refer to: Carpacin 4-(4-Methylphenyl)-4-oxobutanoic acid Myristicin Ocean propanal Quercinol This set index page lists chemical structure...

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Shiso

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chemotypes include eschscholzia ketone, perillene, and the phenylpropanoids myristicin, dillapiole, elemicin, citral, and a type rich in rosefuran.[citation...

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List of psychoactive plants

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Usually referred to as kratom. Has opioid-like and stimulant properties. Myristicin Myristica fragrans Nutmeg Aporphine Nelumbo nucifera Sacred lotus Nepetalactone...

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Piper aduncum

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although phenylpropanoid dillapiole is the most cited component, followed by myristicin, 1,8-cineole and β-ocimene. The essential oil of P. aduncum was considered...

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Psychotomimetism

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Methylenedioxypyrovalerone (MDPV) Methylone Methylphenidate Montelukast Myristicin N-Ethylpentylone Pentazocine Phencyclidine (PCP) Phentermine Pramipexole...

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List of psychedelic drugs

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Piperazines, such as pFPP and TFMPP, usually classified as stimulants Myristicin† and elemicin†, the active constituents of nutmeg Cryogenine (Vertine)†...

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