classified as a list 1 drug per the opium law. production, trade and possession of dmt are prohibited. russia – classified as a schedule i narcotic, including its derivatives (see sumatriptan and zolmitriptan). serbia – dmt, along with stereoisomers and salts is classified as list 4 (psychotropic substances) substance according to act on control of psychoactive substances. sweden – dmt is considered a schedule 1 drug. the swedish supreme court concluded in 2018 that possession of processed plant material containing a significant amount of dmt is illegal. however, possession of unprocessed such plant material was ruled legal. united kingdom – dmt is classified as a class a drug. belgium – dmt cannot be possessed, sold, purchased or imported. usage is not specifically prohibited, but since usage implies possession one could be prosecuted that way. north america canada – dmt is classified as a schedule iii drug under the controlled drugs and substances act, but is legal for religious groups to use. as of 2022 dmt has been decriminalized in vancouver, and there are now several outlets which openly sell this substance in numerous forms. in 2017 the santo daime church céu do montréal received religious exemption to use ayahuasca as a sacrament in their rituals. united states – dmt is classified in the united states as a schedule i drug under the controlled substances act of 1970. in december 2004, the supreme court lifted a stay, thereby allowing the brazil-based união do vegetal (udv) church to use a decoction containing dmt in their christmas services that year. this decoction is a tea made from boiled leaves and vines, known as hoasca within the udv, and ayahuasca in different cultures. in gonzales v. o centro espírita beneficente união do vegetal, the supreme court heard arguments on 1 november 2005, and unanimously ruled in february 2006 that the u.s. federal government must allow the udv to import and consume the tea for religious ceremonies under the 1993 religious freedom restoration act. in september 2008, the three santo daime churches filed suit in federal court to gain legal status to import dmt-containing ayahuasca tea. the case, church of the holy light of the queen v. mukasey, presided over by judge owen m. panner, was ruled in favor of the santo daime church. as of 21 march 2009, a federal judge says members of the church in ashland can import, distribute and brew ayahuasca. u.s. district judge owen panner issued a permanent injunction barring the government from prohibiting or penalizing the sacramental use of "daime tea". panner's order said activities of the church of the holy light of the queen are legal and protected under freedom of religion. his order prohibits the federal government from interfering with and prosecuting church members who follow a list of regulations set out in his order. oceania new zealand – dmt is classified as a class a drug under the misuse of drugs act 1975. australia – dmt is listed as a schedule 9 prohibited substance in australia under the poisons standard (october 2015). a schedule 9 drug is outlined in the poisons act 1964 as "substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the ceo." between 2011 and 2012, the australian federal government was considering changes to the australian criminal code that would classify any plants containing any amount of dmt as "controlled plants". dmt itself was already controlled under current laws. the proposed changes included other similar blanket bans for other substances, such as a ban on any and all plants containing mescaline or ephedrine. the proposal was not pursued after political embarrassment on realisation that this would make the official floral emblem of australia, acacia pycnantha (golden wattle), illegal. the therapeutic goods administration and federal authority had considered a motion to ban the same, but this was withdrawn in may 2012 (as dmt may still hold potential entheogenic value to native and/or religious people). under the misuse of drugs act 1981 6.0 g of dmt is considered enough to determine a court of trial and 2.0 g is considered intent to sell and supply. chemistry dmt crystalsdmt is commonly handled and stored as a hemifumarate, as other dmt acid salts are extremely hygroscopic and will not readily crystallize. its freebase form, although less stable than dmt hemifumarate, is favored by recreational users choosing to vaporize the chemical as it has a lower boiling point. biosynthesis biosynthetic pathway for n,n-dimethyltryptamine dimethyltryptamine is an indole alkaloid derived from the shikimate pathway. its biosynthesis is relatively simple and summarized in the adjacent picture. in plants, the parent amino acid l-tryptophan is produced endogenously where in animals l-tryptophan is an essential amino acid coming from diet. no matter the source of l-tryptophan, the biosynthesis begins with its decarboxylation by an aromatic amino acid decarboxylase (aadc) enzyme (step 1). the resulting decarboxylated tryptophan analog is tryptamine. tryptamine then undergoes a transmethylation (step 2): the enzyme indolethylamine-n-methyltransferase (inmt) catalyzes the transfer of a methyl group from cofactor s-adenosylmethionine (sam), via nucleophilic attack, to tryptamine. this reaction transforms sam into s-adenosylhomocysteine (sah), and gives the intermediate product n-methyltryptamine (nmt). nmt is in turn transmethylated by the same process (step 3) to form the end product n,n-dimethyltryptamine. tryptamine transmethylation is regulated by two products of the reaction: sah, and dmt were shown ex vivo to be among the most potent inhibitors of rabbit inmt activity. this transmethylation mechanism has been repeatedly and consistently proven by radiolabeling of sam methyl group with carbon-14 (14c-ch3)sam. laboratory synthesis dmt can be synthesized through several possible pathways from different starting materials. the two most commonly encountered synthetic routes are through the reaction of indole with oxalyl chloride followed by reaction with dimethylamine and reduction of the carbonyl functionalities with lithium aluminium hydride to form dmt. the second commonly encountered route is through the n,n-dimethylation of tryptamine using formaldehyde followed by reduction with sodium cyanoborohydride or sodium triacetoxyborohydride. sodium borohydride can be used but requires a larger excess of reagents and lower temperatures due to it having a higher selectivity for carbonyl groups as opposed to imines. procedures using sodium cyanoborohydride and sodium triacetoxyborohydride (presumably created in situ from cyanoborohydride though this may not be the case due to the presence of water or methanol) also result in the creation of cyanated tryptamine and beta-carboline byproducts of unknown toxicity while using sodium borohydride in absence of acid does not. bufotenine, a plant extract, can also be synthesized into dmt. alternatively methyl iodide can be used but this results in the creation of a quaternary ammonium salt which must be transformed back into a tertiary amine. clandestine manufacture dmt during various stages of purification in a clandestine setting, dmt is not typically synthesized due to the lack of availability of the starting materials, namely tryptamine and oxalyl chloride. instead, it is more often extracted from plant sources using a nonpolar hydrocarbon solvent such as naphtha or heptane, and a base such as sodium hydroxide. alternatively, an acid-base extraction is sometimes used instead. a variety of plants contain dmt at sufficient levels for being viable sources, but specific plants such as mimosa tenuiflora, acacia acuminata and acacia confusa are most often used. the chemicals involved in the extraction are commonly available. the plant material may be illegal to procure in some countries. the end product (dmt) is illegal in most countries. evidence in mammals published in science in 1961, julius axelrod found an n-methyltransferase enzyme capable of mediating biotransformation of tryptamine into dmt in a rabbit's lung. this finding initiated a still ongoing scientific interest in endogenous dmt production in humans and other mammals. from then on, two major complementary lines of evidence have been investigated: localization and further characterization of the n-methyltransferase enzyme, and analytical studies looking for endogenously produced dmt in body fluids and tissues. in 2013, researchers reported dmt in the pineal gland microdialysate of rodents. a study published in 2014 reported the biosynthesis of n,n-dimethyltryptamine (dmt) in the human melanoma cell line sk-mel-147 including details on its metabolism by peroxidases. it is assumed that more than half of the amount of dmt produced by the acidophilic cells of the pineal gland is secreted before and during death, the amount being 2.5–3.4 mg/kg. however, this claim by strassman has been criticized by david nichols who notes that dmt does not appear to be produced in any meaningful amount by the pineal gland. removal or calcification of the pineal gland does not induce any of the symptoms caused by removal of dmt. the symptoms presented are consistent solely with reduction in melatonin, which is the pineal gland's known function. nichols instead suggests that dynorphin and other endorphins are responsible for the reported euphoria experienced by patients during a near-death experience. in 2014, researchers demonstrated the immunomodulatory potential of dmt and 5-meo-dmt through the sigma-1 receptor of human immune cells. this immunomodulatory activity may contribute to significant anti-inflammatory effects and tissue regeneration. endogenous dmt n,n-dimethyltryptamine (dmt), a psychedelic compound identified endogenously in mammals, is biosynthesized by aromatic l-amino acid decarboxylase (aadc) and indolethylamine-n-methyltransferase (inmt). studies have investigated brain expression of inmt transcript in rats and humans, coexpression of inmt and aadc mrna in rat brain and periphery, and brain concentrations of dmt in rats. inmt transcripts were identified in the cerebral cortex, pineal gland, and choroid plexus of both rats and humans via in situ hybridization. notably, inmt mrna was colocalized with aadc transcript in rat brain tissues, in contrast to rat peripheral tissues where there existed little overlapping expression of inmt with aadc transcripts. additionally, extracellular concentrations of dmt in the cerebral cortex of normal behaving rats, with or without the pineal gland, were similar to those of canonical monoamine neurotransmitters including serotonin. a significant increase of dmt levels in the rat visual cortex was observed following induction of experimental cardiac arrest, a finding independent of an intact pineal gland. these results show for the first time that the rat brain is capable of synthesizing and releasing dmt at concentrations comparable to known monoamine neurotransmitters and raise the possibility that this phenomenon may occur similarly in human brains. the first claimed detection of mammalian endogenous dmt was published in june 1965: german researchers f. franzen and h. gross report to have evidenced and quantified dmt, along with its structural analog bufotenin (5-ho-dmt), in human blood and urine. in an article published four months later, the method used in their study was strongly criticized, and the credibility of their results challenged. few of the analytical methods used prior to 2001 to measure levels of endogenously formed dmt had enough sensitivity and selectivity to produce reliable results. gas chromatography, preferably coupled to mass spectrometry (gc-ms), is considered a minimum requirement. a study published in 2005 implements the most sensitive and selective method ever used to measure endogenous dmt: liquid chromatography–tandem mass spectrometry with electrospray ionization (lc-esi-ms/ms) allows for reaching limits of detection (lods) 12 to 200 fold lower than those attained by the best methods employed in the 1970s. the data summarized in the table below are from studies conforming to the abovementioned requirements (abbreviations used: csf = cerebrospinal fluid; lod = limit of detection; n = number of samples; ng/l and ng/kg = nanograms (10−9 g) per litre, and nanograms per kilogram, respectively): dmt in body fluids and tissues (nb: units have been harmonized) species sample results human blood serum < lod (n = 66) blood plasma < lod (n = 71) ♦ < lod (n = 38); 1,000 & 10,600 ng/l (n = 2) whole blood < lod (n = 20); 50–790 ng/l (n = 20) urine < 100 ng/l (n = 9) ♦ < lod (n = 60); 160–540 ng/l (n = 5) ♦ detected in n = 10 by gc-ms feces < 50 ng/kg (n = 12); 130 ng/kg (n = 1) kidney 15 ng/kg (n = 1) lung 14 ng/kg (n = 1) lumbar csf 100,370 ng/l (n = 1); 2,330–7,210 ng/l (n = 3); 350 & 850 ng/l (n = 2) rat kidney 12 &16 ng/kg (n = 2) lung 22 & 12 ng/kg (n = 2) liver 6 & 10 ng/kg