n,n-dimethyltryptamine n,n-dimethyltryptamine n,n-dimethyltryptamine (dmt or n,n-dmt, spl026) is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine. dmt is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen. n,n-dimethyltryptamineclinical dataroutes ofadministrationoral (with an maoi), vaporized, insufflated, rectal, im, ivatc codenonelegal statuslegal status au: s8 (controlled drug) br: class f (prohibited substances) ca: schedule iii de: anlage i (authorized scientific use only) uk: class b us: schedule i un: psychotropic schedule i identifiers iupac name 2-(1h-indol-3-yl)-n,n-dimethylethanamine cas number61-50-6 ypubchem cid6089iuphar/bps141drugbankdb01488 ychemspider5864 yuniiwub601bhaakeggc08302 ychebichebi:28969 ychemblchembl12420 ycomptox dashboard (epa)dtxsid60110053 echa infocard100.000.463 chemical and physical dataformulac12h16n2molar mass188.274 g·mol−13d model (jsmol)interactive imagedensity1.099 g/cm3melting point40 °c (104 °f)boiling point160 °c (320 °f) at 0.6 torr (80 pa)also reported as80–135 °c (176–275 °f) at 0.03 torr (4.0 pa) smiles cn(ccc1=cnc2=c1c=cc=c2)c inchi inchi=1s/c12h16n2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13h,7-8h2,1-2h3 ykey:dmulvchrpcffgv-uhfffaoysa-n y (verify) part of a series onpsychedelia arts psychedelic art algorithmic art cyberdelic diffraction fractal art liquid light show lsd art paisley phosphene psychedelic music acid house acid jazz acid rock acid techno acid trance chillwave hypnagogic pop madchester neo-psychedelia palm desert scene peyote song p-funk psychedelic folk psychedelic funk psychedelic pop psychedelic rock psychedelic soul psychedelic trance space rock stoner rock trip hop psychedelic film acid western stoner film psychedelic literature culture counterculture entheogen smart shop trip sitter psychedelic microdosing drugs 25i-nbome 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rapid onset, intense effects, and a relatively short duration of action. for those reasons, dmt was known as the "businessman's trip" during the 1960s in the united states, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as lsd or psilocybin mushrooms. dmt can be inhaled, ingested, or injected and its effects depend on the dose, as well as the mode of administration. when inhaled or injected, the effects last a short period of time: about five to 15 minutes. effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor (maoi), such as the ayahuasca brew of many native amazonian tribes. dmt can produce vivid "projections" of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms. dmt is a functional analog and structural analog of other psychedelic tryptamines such as o-acetylpsilocin (4-aco-dmt), psilocybin (4-po-dmt), psilocin (4-ho-dmt), o-methylbufotenin (5-meo-dmt), and bufotenin (5-ho-dmt). parts of the structure of dmt occur within some important biomolecules like serotonin and melatonin, making them structural analogs of dmt. human consumption dmt is produced in many species of plants often in conjunction with its close chemical relatives 5-methoxy-n,n-dimethyltryptamine (5-meo-dmt) and bufotenin (5-oh-dmt). dmt-containing plants are commonly used in indigenous amazonian shamanic practices. it is usually one of the main active constituents of the drink ayahuasca; however, ayahuasca is sometimes brewed with plants that do not produce dmt. it occurs as the primary psychoactive alkaloid in several plants including mimosa tenuiflora, diplopterys cabrerana, and psychotria viridis. dmt is found as a minor alkaloid in snuff made from virola bark resin in which 5-meo-dmt is the main active alkaloid. dmt is also found as a minor alkaloid in bark, pods, and beans of anadenanthera peregrina and anadenanthera colubrina used to make yopo and vilca snuff, in which bufotenin is the main active alkaloid. psilocin and its precursor psilocybin, an active chemical in many psilocybin mushrooms, are structurally similar to dmt. the psychotropic effects of dmt were first studied scientifically by the hungarian chemist and psychologist stephen szára, who performed research with volunteers in the mid-1950s. szára, who later worked for the united states national institutes of health, had turned his attention to dmt after his order for lsd from the swiss company sandoz laboratories was rejected on the grounds that the powerful psychotropic could be dangerous in the hands of a communist country. dmt is generally not active orally unless it is combined with a monoamine oxidase inhibitor such as a reversible inhibitor of monoamine oxidase a (rima), for example, harmaline. without a maoi, the body quickly metabolizes orally administered dmt, and it therefore has no hallucinogenic effect unless the dose exceeds the body's monoamine oxidase's metabolic capacity. other means of consumption such as vaporizing, injecting, or insufflating the drug can produce powerful hallucinations for a short time (usually less than half an hour), as the dmt reaches the brain before it can be metabolized by the body's natural monoamine oxidase. taking an maoi prior to vaporizing or injecting dmt prolongs and enhances the effects. clinical use research dimethyltryptamine (dmt), an endogenous ligand of sigma-1 receptors (sig-1rs), acts against systemic hypoxia. research demonstrates dmt reduces the number of apoptotic and ferroptotic cells in mammalian forebrain and supports astrocyte survival in an ischemic environment. according to these data, dmt may be considered as adjuvant pharmacological therapy in the management of acute cerebral ischemia. dmt is studied as a potential treatment for parkinson’s disease in a phase 1/2 clinical trial. spl026 (dmt fumarate) is currently undergoing phase ii clinical trials investigating its use alongside supportive psychotherapy as a potential treatment major depressive disorder. additionally, a safety study is underway to investigate the effects of combining ssris with spl026. neuropharmocology recently, researchers discovered that n,n-dimethyltryptamine is a potent psychoplastogen, a compound capable of promoting rapid and sustained neuroplasticity that may have wide-ranging therapeutic benefit. quantities of dimethyltryptamine and o-methylbufotenin were found present in the cerebrospinal fluid of humans in a psychiatric study. effects subjective psychedelic experiences induced dmt experiences can include profound time-dilatory, visual, auditory, tactile, and proprioceptive distortions and hallucinations, and other experiences that, by most firsthand accounts, defy verbal or visual description. examples include perceiving hyperbolic geometry or seeing escher-like impossible objects. several scientific experimental studies have tried to measure subjective experiences of altered states of consciousness induced by drugs under highly controlled and safe conditions. rick strassman and his colleagues conducted a five-year-long dmt study at the university of new mexico in the 1990s. the results provided insight about the quality of subjective psychedelic experiences. in this study participants received the dmt dosage via intravenous injection and the findings suggested that different psychedelic experiences can occur, depending on the level of dosage. lower doses (0.01 and 0.05 mg/kg) produced some aesthetic and emotional responses, but not hallucinogenic experiences (e.g., 0.05 mg/kg had mild mood elevating and calming properties). in contrast, responses produced by higher doses (0.2 and 0.4 mg/kg) researchers labeled as "hallucinogenic" that elicited "intensely colored, rapidly moving display of visual images, formed, abstract or both". comparing to other sensory modalities the most affected was the visual. participants reported visual hallucinations, fewer auditory hallucinations and specific physical sensations progressing to a sense of bodily dissociation, as well as to experiences of euphoria, calm, fear, and anxiety. these dose-dependent effects match well with anonymously posted "trip reports" online, where users report "breakthroughs" above certain doses. strassman also stressed the importance of the context where the drug has been taken. he claimed that dmt has no beneficial effects of itself, rather the context when and where people take it plays an important role. it appears that dmt can induce a state or feeling where the person believes to "communicate with other intelligent lifeforms" (see "machine elves"). high doses of dmt produce a state that involves a sense of "another intelligence" that people sometimes describe as "super-intelligent", but "emotionally detached". a 1995 study by adolf dittrich and daniel lamparter found that the dmt-induced altered state of consciousness (asc) is strongly influenced by habitual rather than situative factors. in the study, researchers used three dimensions of the apz questionnaire to examine asc. the first dimension, oceanic boundlessness (ob), refers to dissolution of ego boundaries and is mostly associated with positive emotions. the second dimension, anxious ego-dissolution (aed), represents a disordering of thoughts and decreases in autonomy and self-control. last, visionary restructuralization (vr) refers to auditory/visual illusions and hallucinations. results showed strong effects within the first and third dimensions for all conditions, especially with dmt, and suggested strong intrastability of elicited reactions independently of the condition for the ob and vr scales. reported encounters with external entities entities perceived during dmt inebriation have been represented in diverse forms of psychedelic art. the term machine elf was coined by ethnobotanist terence mckenna for the entities he encountered in dmt "hyperspace", also using terms like fractal elves, or self-transforming machine elves. mckenna first encountered the "machine elves" after smoking dmt in berkeley in 1965. his subsequent speculations regarding the hyperdimensional space in which they were encountered have inspired a great many artists and musicians, and the meaning of dmt entities has been a subject of considerable debate among participants in a networked cultural underground, enthused by mckenna's effusive accounts of dmt hyperspace. cliff pickover has also written about the "machine elf" experience, in the book sex, drugs, einstein, & elves. strassman noted similarities between self-reports of his dmt study participants' encounters with these "entities", and mythological descriptions of figures such as ḥayyot haq-qodesh in ancient religions, including both angels and demons. strassman also argues for a similarity in his study participants' descriptions of mechanized wheels, gears and machinery in these encounters, with those described in visions of encounters with the living creatures and ophanim of the hebrew bible, noting they may stem from a common neuropsychopharmacological experience. strassman argues that the more positive of the "external entities" encountered in dmt experiences should be understood as analogous to certain forms of angels: the medieval jewish philosophers whom i rely upon for understanding the hebrew bible text and its concept of prophecy portray angels as god's intermediaries. that is, they perform a certain function for god. within the context of my dmt research, i believe that the beings that volunteers see could be conceived of as angelic – that is, previously invisible, incorporeal spiritual forces that are engarbed or enclothed in a particular form – determined by the psychological and spiritual development of the volunteers – bringing a particular message or experience to that volunteer. strassman's experimental participants also note that some other entities can subjectively resemble creatures more like insects and aliens. as a result, strassman writes these experiences among his experimental participants "also left me feeling confused and concerned about where the spirit molecule was leading us. it was at this point that i began to wonder if i was getting in over my head with this research." hallucinations of strange creatures had been reported by stephen szara in a 1958 study in psychotic patients, in which he described how one of his subjects under the influence of dmt had experienced "strange creatures, dwarves or something" at the beginning of a dmt trip. other researchers of the entities seemingly encountered by dmt users describe them as "entities" or "beings" in humanoid as well as animal form, with descriptions of "little people" being common (non-human gnomes, elves, imps, etc.). strassman and others have speculated that this form of hallucination may be the cause of alien abduction and extraterrestrial encounter experiences, which may occur through endogenously-occurring dmt. likening them to descriptions of rattling and chattering auditory phenomena described in encounters with the hayyoth in the book of ezekiel, rick strassman notes that participants in his studies, when reporting encounters with the alleged entities, have also described loud auditory hallucinations, such as one subject reporting typically "the elves laughing or talking at high volume, chattering, twittering". near-death experience a 2018 study found significant relationships between a dmt experience and a near-death experience. a 2019 large-scale study pointed that ketamine, salvia divinorum, and dmt (and