3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy, and molly, is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.
PiHKAL: A Chemical Love Story is a book by Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved".
Empathogens or entactogens are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA). This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulants. Major members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, GHB, αMT, and αET, MDAI among others. Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines. When referring to MDMA and its counterparts, the term MDxx is often used. Entactogens are sometimes incorrectly referred to as hallucinogens or stimulants, although many entactogens such as ecstasy exhibit psychedelic or stimulant properties as well.
3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.
MBDB, also known as N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA. It is known by the street names "Eden" and "Methyl-J".
Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.
Zolazepam (Flupyrazapon) is a pyrazolodiazepinone derivative structurally related to the benzodiazepine drugs, which is used as an anaesthetic for a wide range of animals in veterinary medicine. Zolazepam is usually administered in combination with other drugs such as the NMDA antagonist tiletamine or the α2 adrenergic receptor agonist xylazine, depending on what purpose it is being used for. It is 5-10 times the potency of diazepam.
Amifampridine is used as a drug, predominantly in the treatment of a number of rare muscle diseases. The free base form of the drug has been used to treat congenital myasthenic syndromes and Lambert–Eaton myasthenic syndrome (LEMS) through compassionate use programs since the 1990s and was recommended as a first line treatment for LEMS in 2006, using ad hoc forms of the drug, since there was no marketed form.
Ganesha (2,5-dimethoxy-3,4-dimethylamphetamine) is a lesser-known psychedelic drug. It is also a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 24–32 mg. The drug is usually taken orally, although other routes such as rectally may also be used. Ganesha is synthesized from 2,5-dimethoxy-3,4-dimethylbenzaldehyde. Ganesha is the amphetamine analog of 2C-G. It is a particularly long lasting drug, with the duration listed in PiHKAL as being 18–24 hours, which might make it undesirable to some users. It is named after the Hindu deity, Ganesha. Very little is known about the dangers or toxicity of ganesha. Effects of ganesha include:
3,4-Methylenedioxy-N-methylphentermine is a lesser-known psychedelic drug. MDMP was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 110 mg, and the duration is listed as approximately 6 hours. MDMP produces few to no effects, and is slightly similar to MDMA. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDMP.
Methylenedioxybutylamphetamine is a lesser-known psychedelic drug. It is also the N-butyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDBU was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 40 mg, and the duration unknown. MDBU produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDBU.
Methylenedioxybenzylamphetamine, abbreviated MDBZ, and systematically named 3,4-methylenedioxy-N-benzylamphetamine, is a psychedelic drug. It is the N-benzyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDBZ was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 150 mg, and the duration unknown. Very few data exist about the pharmacological properties, metabolism, and toxicity of MDBZ.
ALPHA (alpha-ethyl-3,4-methylenedioxybenzylamine) is a lesser-known psychedelic drug and a substituted benzylamine. It is also the benzylamine analog of 3,4-methylenedioxyamphetamine (MDA). ALPHA was first synthesized by Alexander Shulgin. In his book PIHKAL on the MDA page, the threshold dosage is listed as 10 mg. At mild threshold dosages there are eyes-closed "dreams" with some body tingling, at higher doses was reported to produce a pleasant, positive feeling. This compound is not anoretic at any dose. It lasts about 3 hours. Very little data exists about the pharmacological properties, metabolism, and toxicity of ALPHA.
Catalyst Pharmaceuticals, Inc. is a biopharmaceutical company based in Coral Gables, Florida, United States. The company develops medicines for rare diseases, including the phosphate salt of amifampridine for the treatment of Lambert–Eaton myasthenic syndrome (LEMS). The drug is referred to under the trade name Firdapse, which was approved by the FDA for approved use in children 6 years and older with LEMS in addition to the prior approval for use in adults with LEMS on November 28, 2018. Firdapse commercially launched in January 2019.
25I-NB34MD (NB34MD-2C-I) is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a potent partial agonist for the human 5-HT2A receptor, and presumably has similar properties to 2C-I. It has a binding affinity of 0.67nM at the human 5-HT2A receptor, making it several times weaker than its positional isomer 25I-NBMD and a similar potency to 25I-NBF.
5-Fluoro-MET (5F-MET, 5-fluoro-N-methyl-N-ethyltryptamine) is a psychedelic tryptamine derivative related to drugs such as 5-Fluoro-DMT and N-methyl-N-ethyltryptamine (MET). It acts as an agonist at the 5-HT2A receptor with an EC50 of 20.6 nM and produces a head-twitch response in animal studies. Ring fluorination in this case increases efficacy at 5-HT2A, with 5F-MET having an efficacy of 87.6% vs 5-HT, vs 36.2% for the partial agonist MET. It is claimed to have antidepressant activity.
5-Fluoro-EPT (5F-EPT, 5-fluoro-N-ethyl-N-propyltryptamine) is a psychedelic tryptamine derivative related to drugs such as EPT and 5-MeO-EPT. It acts as a potent full agonist at the 5-HT2A receptor with an EC50 of 5.54 nM and an efficacy of 104% (compared to serotonin). It produces a head-twitch response in animal studies, and is claimed to have antidepressant activity.
5-TFMO-DMT (5-(trifluoromethoxy)-DMT, 5-OCF3-DMT, 5-(trifluoromethoxy)-N,N-dimethyltryptamine) is a psychedelic tryptamine derivative related to drugs such as 5-MeO-DMT and DMT (DMT). It acts as an agonist at the 5-HT2A receptor with an EC50 of 127.2 nM. It was shown to release serotonin (5-HT) from synaptosomal preparations, and to reduce immobility time in the forced-swim test in animal studies, suggesting that it might have antidepressant activity.
GM-2505 is a psychedelic and experimental antidepressant that acts as a 5-HT2A and 5-HT2C receptor agonist and serotonin releasing agent. Compared to other 5-HT2A receptor agonists, it is said to have a shorter duration of action. It is under development by Gilgamesh Pharmaceuticals. As of March 2024, GM-2505 is in phase 2 clinical trials for the treatment of major depressive disorder. The chemical structure of GM-2505 does not yet seem to have been disclosed, but disclosed compounds with the same mechanism of action have been patented by Gilgamesh in 2022.
