Portal:Phenethylamines
Portal maintenance status: (October 2018)
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Introduction
R2=R3=R4=R5=R6=RN=Rα=Rβ=H.
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.
The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an amino (NH) group via a two-carbon sidechain. Hence, any substituted phenethylamine can be classified according to the substitution of hydrogen (H) atoms on phenethylamine's phenyl ring, sidechain, or amino group with a specific group of atoms.
Selected general articles
25I-NBOMe (2C-I-NBOMe, Cimbi-5, also shortened to "25I") is a psychedelic hallucinogen that is used in biochemistry research for mapping the brain's usage of the type 2A serotonin receptor; it is also sometimes used for recreational purposes. It is derivative of the substituted phenethylamine 2C-I and is the most well-known member of the 25-NB family. It was discovered in 2003 by chemist Ralf Heim at the Free University of Berlin, who published his findings in his PhD dissertation. The compound was subsequently investigated by a team at Purdue University led by David Nichols.
The carbon-11 labelled version of 25I-NBOMe, [11C]Cimbi-5, was synthesized and validated as a radiotracer for positron emission tomography (PET) in Copenhagen. Being the first 5-HT2A receptor full agonist PET radioligand, [11C]-CIMBI-5 shows promise as a more functional marker of these receptors, particularly in their high affinity states. Read more...
AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). It is described by Alexander Shulgin in the book TiHKAL (Tryptamines i Have Known And Loved). It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant. Read more...
Droxidopa (INN; trade name Northera; also known as L-DOPS, L-threo-dihydroxyphenylserine, L-threo-DOPS and SM-5688) is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitter norepinephrine (noradrenaline). Unlike norepinephrine, droxidopa is capable of crossing the protective blood–brain barrier (BBB). Read more...
1,3-Benzodioxolyl-N-methylbutanamine (N-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. It is known by the street names Eden and Methyl-J. MBDB is a closely related chemical analogue of MDMA, with the only difference between the two molecules being an ethyl group instead of a methyl group attached to the alpha carbon. It has IC50 values of 784 nM against 5-HT, 7825 nM against dopamine, and 1233 nM against norepinephrine. Its metabolism has been described in scientific literature.
MBDB was first synthesized by pharmacologist and medicinal chemist David E. Nichols and later tested by Alexander Shulgin and described in his book, PiHKAL: A Chemical Love Story. MBDB's dosage, according to PiHKAL, is 180–210 mg; the proper dosage relative to body mass seems unknown. Its duration is 4–6 hours, with noticeable after-effects lasting for 1–3 hours. Read more...
Tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. It is called tyrosyl when referred to as a functional group or side chain. While tyrosine is generally classified as a hydrophobic amino acid, it is more hydrophilic than phenylalanine. It is encoded by the codons UAC and UAU in messenger RNA. Read more...
para-Methoxyamphetamine (PMA; "Death", "Dr. Death"), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.
PMA has been found in tablets touted as MDMA (ecstasy) although its effects are markedly different compared to those of MDMA. The consequences of such deception have often included hospitalization and death for unwitting users. PMA is commonly synthesized from anethole, the flavor compound of anise and fennel, mainly because the starting material for MDMA, safrole, has become less available due to law enforcement action, causing illicit drug manufacturers to use anethole as an alternative. Read more...
Synephrine, or, more specifically, p-synephrine, is an alkaloid, occurring naturally in some plants and animals, and also in approved drugs products as its m-substituted analog known as neo-synephrine. p-Synephrine (or formerly Sympatol and oxedrine [BAN]) and m-synephrine are known for their longer acting adrenergic effects compared to norepinephrine. This substance is present at very low concentrations in common foodstuffs such as orange juice and other orange (Citrus species) products, both of the "sweet" and "bitter" variety. The preparations used in traditional Chinese medicine (TCM), also known as Zhi Shi, are the immature and dried whole oranges from Citrus aurantium (Fructus Aurantii Immaturus). Extracts of the same material or purified synephrine are also marketed in the US, sometimes in combination with caffeine, as a weight-loss-promoting dietary supplement for oral consumption. While the traditional preparations have been in use for millennia as a component of TCM-formulas, synephrine itself is not an approved OTC drug. As a pharmaceutical, m-synephrine is still used as a sympathomimetic (i.e. for its hypertensive and vasoconstrictor properties), mostly by injection for the treatment of emergencies such as shock, and rarely orally for the treatment of bronchial problems associated with asthma and hay-fever.
It is important to distinguish between studies concerning synephrine as a single chemical entity (synephrine can exist in the form of either of two stereoisomers, d- and l-synephrine, which are chemically and pharmacologically distinct), and synephrine which is mixed with other drugs and/or botanical extracts in a "Supplement", as well as synephrine which is present as only one chemical component in a naturally-occurring mixture of phytochemicals such as the rind or fruit of a bitter orange. Mixtures containing synephrine as only one of their chemical components (regardless of whether these are of synthetic or natural origin) should not be assumed to produce exactly the same biological effects as synephrine alone. Read more...
4-Methylthioamphetamine (4-MTA) is a designer drug of the substituted amphetamine class developed in the 1990s by a team led by David E. Nichols, an American pharmacologist and medical chemist, at Purdue University. It acts as a non-neurotoxic highly selective serotonin releasing agent (SSRA) in animals. 4-MTA is the methylthio derivative of amphetamine. Read more...
Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine, and AN-1; brand name Aponeuron) is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity, ADHD, and narcolepsy. It has largely been withdrawn from clinical use following problems with abuse. The drug is a prodrug to amphetamine. Read more...
4-Fluoroamphetamine (4-FA; 4-FMP; PAL-303; "Flux"), also known as para-fluoroamphetamine (PFA) is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects, and is described subjectively as being between amphetamine and MDMA. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine. Read more...
Xylopropamine (Perhedrin, Esanin), also known as 3,4-dimethylamphetamine, is a stimulant drug of the phenethylamine and amphetamine classes which was developed and marketed as an appetite suppressant in the 1950s.
Xylopropamine was briefly sold as the sulfate salt, but it was not widely marketed. Other related amphetamine derivatives such as 2,4-dimethylamphetamine were also investigated for the same purpose, however these drugs had negative side effects such as high blood pressure and were not very successful, mainly due to the introduction of alternative drugs like phentermine which had similar efficacy but fewer side effects. Read more...
3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine. Read more...
Ψ-DOM, or 2,6-dimethoxy-4-methylamphetamine, is a hallucinogenic, psychedelic drug and a structural isomer of the better-known hallucinogen DOM. Ψ-DOM was first reported by Alexander Shulgin in his book PiHKAL (Phenethylamines i Have Known And Loved).
Ψ-DOM has similar effects to DOM, but is only around 1/3 - 1/2 the potency, with an active dose reported to be between 15-25 milligrams. The effects of Ψ-DOM last for around 6–8 hours. Read more...
Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.
There have been several unconfirmed reports of lysergic acid 2,4-dimethylazetidide being synthesized in illicit laboratories and distributed on blotter paper or in liquid solution under names such as "diazedine" and "λ". Read more...
Bupropion, sold under the brand names Wellbutrin and Zyban among others, is a medication primarily used as an antidepressant and smoking cessation aid. It is an effective antidepressant on its own, but is also used as an add-on medication in cases of incomplete response to first-line SSRI antidepressants. Bupropion is taken in tablet form and is available only by prescription in most countries.
Common side effects include dry mouth, trouble sleeping, agitation, and headaches. Serious side effects include an increased risk for epileptic seizures, which caused the drug to be withdrawn from the market for some time and then the recommended dose to be reduced. In comparison to some other antidepressants, it does not cause as much sexual dysfunction or sleepiness, and may result in weight loss. It is unclear if use during pregnancy is safe. Read more...
5-APB (abbreviation of "5-(2-aminopropyl)benzofuran"; see infobox for the correct IUPAC name) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-APB and other compounds are sometimes informally called "Benzofury".
5-APB is commonly found as the succinate and hydrochloride salt. The hydrochloride salt is 10% more potent by mass and doses should be adjusted accordingly. Read more...
Ephenidine (also known as NEDPA and EPE) is a dissociative anesthetic that has been sold online as a designer drug. It is illegal in some countries as a structural isomer of the banned opioid drug lefetamine, but has been sold in countries where it is not yet banned. Read more...
Isoetarine is a selective short-acting β2 adrenoreceptor agonist. It can be called the "granddaughter of adrenalin" in the line of β2 agonists that gave quick relief for bronchospasm and asthma. Epinephrine (adrenalin) was the first of these, and next came isoprenaline (isoproterenol). Isoetharine was the third drug in this line, thus the third generation or granddaughter of the original.
In the western US it was the drug of choice in the late 1970s and early 1980s for nebulization ("breathing treatment") to relieve airway spasm. It generally gave sharp relief of shortness of breath, starting within two to five minutes after the patient began breathing the nebulized mist. This rapid onset is not as clearly present in later drugs. Read more...
6-Fluoronorepinephrine (6-FNE) is a selective α1 and α2 adrenergic receptor full agonist related to norepinephrine. It is the only selective full agonist for the α adrenergic receptors known to date and has been used to study their function in scientific research. Infusion of 6-FNE into the locus coeruleus of rodents produces marked hyperactivity and behavioral disinhibition by suppressing activity in the area via stimulation of α1 adrenergic receptors. Read more...
Proscaline, or 4-propoxy-3,5-DMPEA, is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline, isoproscaline, and escaline. Read more...
Metirosine (INN and BAN; α-Methyltyrosine, Metyrosine USAN, AMPT) is an antihypertensive drug. It inhibits the enzyme tyrosine hydroxylase and, therefore, catecholamine synthesis, which, as a consequence, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body. Read more...
Iofetamine (iodine-123, 123I), brand names Perfusamine, SPECTamine), or N-isopropyl-(123I)-p-iodoamphetamine (IMP), is a lipid-soluble amine and radiopharmaceutical drug used in cerebral blood perfusion imaging with single photon emission computed tomography (SPECT). Labeled with the radioactive isotope iodine-123, it is approved for use in the United States as a diagnostic aid in determining the localization of and in the evaluation of non-lacunar stroke and complex partial seizures, as well as in the early diagnosis of Alzheimer's disease.
An analogue of amphetamine, iofetamine has shown to inhibit the reuptake of serotonin and norepinephrine as well as induce the release of these neurotransmitters and of dopamine with similar potencies to other amphetamines like d-amphetamine and p-chloroamphetamine. In addition, on account of its high lipophilicity, iofetamine rapidly penetrates the blood-brain-barrier. Accordingly, though not known to have been reported in the medical literature, iofetamine likely possesses psychostimulant and possibly entactogenic effects. However, based on structure-activity relationships, it may also be highly neurotoxic to serotonergic and dopaminergic neurons similarly to most other para-halogenated amphetamines. Read more...
Pseudoephedrine (/ˌsjuːdoʊ.ɪˈfɛdrɪn,-ˈɛfɪdriːn/; PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses.
The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations, either as a single ingredient or (more commonly) in combination with antihistamines, guaifenesin, dextromethorphan, and/or paracetamol (acetaminophen) or an NSAID (such as aspirin or ibuprofen). Read more...
Hordenine (N,N-dimethyltyramine) is an alkaloid of the phenethylamine class that occurs naturally in a variety of plants, taking its name from one of the most common, barley (Hordeum species). Chemically, hordenine is the N-methyl derivative of N-methyltyramine, and the N,N-dimethyl derivative of the well-known biogenic amine tyramine, from which it is biosynthetically derived and with which it shares some pharmacological properties (see below). Currently, hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the central nervous system, and has the ability to promote weight loss by enhancing metabolism. In experimental animals, given sufficiently large doses parenterally (i.e. by injection), hordenine does produce an increase in blood pressure, as well as other disturbances of the cardiovascular, respiratory, and nervous systems. These effects are generally not reproduced by oral administration of the drug in test animals, and virtually no scientific reports of the effects of hordenine in human beings have been published. Read more...
2,5-Dimethoxy-4-ethylamphetamine (DOET, DOE, Hecate) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved). Read more...
Alfetamine, or alpha-allyl-phenethylamine, is a chemical compound of the phenethylamine family. It was briefly investigated as a possible antidepressant in the early 1970s. Its activity profile was said to be very similar to imipramine and amitriptyline, two tricyclic antidepressants. Read more...
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The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when
R2=R3=R4=R5=R6=RN=Rα=Rβ=H.
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