myristicin myristicin 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 effectiveness of other insecticides. when ingested, myristicin may produce hallucinogenic effects, and can be converted to mmdma in controlled chemical synthesis. it interacts with many enzymes and signaling pathways in the body, and may have dose-dependent cytotoxicity in living cells. myristicinclinical dataother names3-methoxy-4,5-methylenedioxy-allylbenzene; 5-methoxy-3,4-methylenedioxy-allylbenzenedependenceliabilitylow/none / not typicaladdictionliabilitylowroutes ofadministrationorallegal statuslegal status in general: uncontrolled, could be illegal in the uk under the psychoactive substances act 2016 if is sold for human consumption or synthetized for recreational use. identifiers iupac name 7-allyl-5-methoxy-1,3-benzodioxole cas number607-91-0 ypubchem cid4276chemspider4125 yunii04pd6ct78wkeggc10480 ychemblchembl481044 ycomptox dashboard (epa)dtxsid1025693 echa infocard100.009.225 chemical and physical dataformulac11h12o3molar mass192.214 g·mol−13d 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 ykey:bnwjohglibdbob-uhfffaoysa-n y (verify) uses isolated myristicin has proven an effective insecticide against many agricultural pests, including aedes aegypti mosquito larvae, spilosoma obliqua (hairy caterpillars), epilachna varivestis (mexican bean beetles), acyrthosiphon pisum (pea aphids), mites, and drosophila melanogaster (fruit flies). myristicin was shown to be an effective repellant, and to cause mortality via direct and systemic exposure. it also displayed a synergistic effect when administered to insects in combination with existing insecticides. the structure of myristicin closely resembles that of amphetamine compounds, and it is capable of producing psychotropic effects similar to mdma compounds. because of this, it can be used in synthetic synthesis to create amphetamine derivatives, and create designer drugs like mmdma that are similar in structure and effect to mdma. out of the common spices that contain myristicin, nutmeg has the highest relative concentration of the compound. therefore, it is used most frequently to isolate myristicin or exploit its effects. furthermore, myristicin interferes with multiple signaling pathways and enzyme processes in the body. sources of myristicin myristicin can be found in nutmeg, black pepper, and many members of the umbelliferae family including anise, carrots, parsley, celery, dill, and parsnip. trace amounts have also been isolated from a variety of plant species including ridolfia segetum (harvest fennel), species of the oenanthe genus (water dropworts), species of the lamiaceae family (mint, sage, or deadnettle families), cinnamomum glanduliferum (nepal camphor tree), and piper mullesua ("hill pepper"). depending on the conditions of growth and storage of the plant, a high quality nutmeg (myristica fragrans) seed can contain up to 13 mg of myristicin per 1 gram, or 1.3%. in the isolated essential oils, myristicin constitutes on average 13.24% of nutmeg oil, 6.32% of parsley leaf oil, 7.63% of dill herb oil, and 0.18% of celery seed oil. physiological effects psychoactive effects at a minimum dose of about 5 g of nutmeg powder, symptoms of nutmeg intoxication can begin to emerge. nutmeg intoxication may produce a feeling similar to thc in lower doses. common effects include dizziness, drowsiness, and confusion, although in higher amounts, it may have effects similar to other deliriants due to its hallucinogenic effects. nutmegs weed like high, while partially from myristicin, is also from licarin a and methoxylicarin a. pharmacology myristicin is additionally known to be a weak inhibitor of monoamine oxidase (mao), a liver enzyme in humans that metabolizes neurotransmitters (e.g., serotonin, dopamine, epinephrine, and norepinephrine). it lacks the basic nitrogen atom that is typical of mao inhibitors (maois), potentially explaining a weaker inhibitory effect. while smaller concentrations of maois may not cause problems, there are additional warnings regarding drug interactions. those taking antidepressants that are maois (such as phenelzine, isocarboxazid, tranylcypromine or selegiline) or taking selective serotonin re-uptake inhibiting (ssri) antidepressants should avoid essential oils rich in myristicin, such as that of nutmeg or anise. metabolites myristicin has been noted to be enzymatically hydroxylated into 1'-hydroxymyristicin and enzymatically formed 5-allyl-1-methoxy-2,3-dihydroxybenzene (oxidation of the methylenedioxy group). myristicin is also formed into demethylenylmyristicin, dihydroxymyristicin, and elemicin is formed into o-demethylelemicin, o-demethyldihydroxyelemicin, and safrole to demethylenylsafrole. toxicity myristicin has been proven to be cytotoxic, or toxic to living cells. specifically, it stimulates cytochrome c release, which activates caspase cascades and induces early apoptosis in the cells. myristicin has also been shown to inhibit cytochrome p450 enzymes in humans, which is responsible for metabolizing a variety of substrates including hormones and toxins, allowing these substrates to accumulate. the effects of nutmeg consumed in large doses are attributed mostly to myristicin, where 1–7 hours following ingestion symptoms include disorientation, giddiness, stupor, and/or stimulation of the central nervous system leading to euphoria, mild to intense hallucinations (similar to deliriants, walls and ceiling glitching or breathing), disorientation to time and surroundings, disassociation, feelings of levitation, feeling of fuzziness similar to thc but heavier, head feeling pressurized, loss of consciousness, tachycardia, weak pulse, anxiety, and hypertension. symptoms of nutmeg intoxication further include nausea, abdominal pain, vomiting, minor to severe muscle spasms (severe in extreme overdose), headache, dryness of mouth, mydriasis or miosis, hypotension, shock, and potentially death. myristicin poisoning can be detected by testing levels of myristicin in the blood. there are currently no known antidotes for myristicin poisoning, and treatment focuses on symptom management and potential sedation in cases of extreme delirium or aggravation. chemistry brief overview of chemical synthesis: myristicin to mmdma structural comparison of myristicin, amphetamine and derivatives with a chemical structure resembling amphetamines and other precursors, myristicin can also be used to synthesize illicit hallucinogenic drugs. under controlled conditions, myristicin isolated from nutmeg oil can be converted into mmdma, a synthetic "designer drug" amphetamine derivative that is less potent than mdma but produces comparable stimulant and hallucinogenic effects. myristicin is soluble in ethanol, ether, and acetone, but insoluble in water