Methoxyphenethylamines

Verapamil, sold under various trade names, is a calcium channel blocker medication used for the treatment of high blood pressure, angina (chest pain from not enough blood flow to the heart), and supraventricular tachycardia. It may also be used for the prevention of migraines and cluster headaches. It is given by mouth or by injection into a vein.

Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder. Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD) as a recommended first-line treatment. It may also be used for chronic neuropathic pain. It is taken orally (swallowed by mouth). It is also available as the salt venlafaxine besylate (venlafaxine benzenesulfonate monohydrate) in an exte

Atenolol is a beta blocker medication primarily used to treat high blood pressure and heart-associated chest pain. Although used to treat high blood pressure, it does not seem to improve mortality in those with the condition. Other uses include the prevention of migraines and treatment of certain irregular heart beats. It is taken orally (by mouth) or by intravenous injection (injection into a vein). It can also be used with other blood pressure medications.

Agomelatine, sold under the brand name Thymanax among others, is an atypical antidepressant most commonly used to treat major depressive disorder and generalized anxiety disorder. One review found that it is as effective as other antidepressants with similar discontinuation rates overall but fewer discontinuations due to side effects. Another review also found it was similarly effective to many other antidepressants.

Ivabradine, sold under the brand name Procoralan among others, is a medication, which is a pacemaker current (If) inhibitor, used for the symptomatic management of heart-related chest pain and heart failure. Patients who qualify for use of ivabradine for congestive heart failure are patients who have symptomatic heart failure, with reduced ejection fraction, and heart rate at least 70 bpm, and the condition not able to be fully managed by beta blockers.

Midodrine, sold under the brand name Proamatine among others, is an antihypotensive medication used to treat orthostatic hypotension (low blood pressure when standing) and urinary incontinence. It is taken by mouth.

'''para-Methoxyamphetamine (PMA), 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 entactogenic effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

Metanephrine, also known as metadrenaline, is a metabolite of epinephrine (also known as adrenaline) created by action of catechol-O-methyl transferase on epinephrine. An article in the Journal of the American Medical Association, 2002, indicated that the measurement of plasma free levels of the metanephrines group of molecules (including metanephrine and normetanephrine) is the best tool in the diagnosis of pheochromocytoma, an adrenal medullary neoplasm.

Bevantolol (INN) was a drug candidate for angina and hypertension that acted as both a beta blocker and a calcium channel blocker. It was discovered and developed by Warner-Lambert but in January 1989 the company announced that it had withdrawn the New Drug Application; the company's chairman said: "Who needs the 30th beta blocker?" it wasn't marketed in the US, UK, or Europe and the authors of a Cochrane review could find no product monograph for it.

Normetanephrine, also called normetadrenaline, is a metabolite of norepinephrine created by action of catechol-O-methyl transferase on norepinephrine. It is excreted in the urine and found in certain tissues. It is a marker for catecholamine-secreting tumors such as pheochromocytoma.

3-Methoxytyramine (3-MT), also known as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine and the major metabolite of the monoamine neurotransmitter dopamine. It is formed by the introduction of a methyl group to dopamine by the enzyme catechol-O-methyltransferase (COMT). 3-MT can be further metabolized by the enzyme monoamine oxidase (MAO) to form homovanillic acid (HVA), which is then typically excreted in the urine.

3-Iodothyronamine (T1AM) is an endogenous thyronamine. It is a high-affinity ligand of the trace amine-associated receptor 1 (TAAR1). T1AM is the most potent endogenous TAAR1 agonist yet discovered. It is also an agonist of the TAAR2 and TAAR5 with similar potency as for the TAAR1 (all in the case of the human proteins). T1AM is not a ligand of the thyroid hormone receptors. However, it is additionally a ligand of various monoamine and other receptors. For instance, it is a muscarinic acetylcholine receptor antagonist.

Thyronamine is a type of decarboxylated and deiodinated metabolite of the thyroid hormones thyroxine (T4) and 3,5,3'-triiodothyronine (T3). The word thyronamine can refer to either the family of molecules, or the specific molecule from which they are derived.

Butaxamine (INN; also known as butoxamine) is a β2-selective beta blocker. Its primary use is in experimental situations in which blockade of β2 receptors is necessary to determine the activity of the drug (i.e. if the β2 receptor is completely blocked, but the given effect is still present, the given effect is not a characteristic of the β2 receptor). It has no clinical use. An alternative name is α-(1-[tert-butylamino]ethyl)-2,5-dimethoxybenzyl alcohol.

'''para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA'), is a serotonergic drug of the amphetamine family related to para''-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine.

Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent. It has mostly or entirely been discontinued.

'''3,3',5-Triiodothyronamine''' is a thyronamine.

Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus. It contains an unusual 1,2,3,4,5-benzopentathiepine ring system.

group of stereoisomers

3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or '''O,O-dimethyldopamine''', is a chemical compound of the phenethylamine family. 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 (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).

MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families. It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).

Methoxyphenamine (trade names ASMI, Euspirol, Orthoxine, Ortodrinex, Proasma), also known as '2-methoxy-N-methylamphetamine (OMMA'), is a β-adrenergic receptor agonist of the amphetamine class used as a bronchodilator.

Macromerine, also known as 'β-hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine', is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris. It can also be found in C. runyonii, C. elephantidens, and other related members of the family Cactaceae.

Gallopamil (INN) is an L-type calcium channel blocker that is an analog of verapamil. It is used in the treatment of abnormal heart rhythms.

Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid. It is produced in the opium poppy from the amino acid tyrosine, initially as (S)-reticuline, which is a precursor to alkaloids including papaverine and stylopine. Another large group of alkaloids including morphine are made after (S)-reticuline has been converted in the poppy to its enantiomer, (R)-reticuline.

Ciladopa (developmental code name AY-27,110) is a dopamine agonist with a similar chemical structure to dopamine. It was under investigation as an antiparkinsonian agent but was discontinued due to concerns of tumorogenesis in rodents.

Cutamesine (SA 4503) is a synthetic sigma receptor agonist which is selective for the σ1 receptor, a chaperone protein mainly found in the endoplasmic reticulum of cells in the central nervous system. These σ1 receptors play a key role in the modulation of Ca2+ release and apoptosis. Cutamesine's activation of the σ1 receptor is tied to a variety of physiological phenomena in the CNS, including activation of dopamine-releasing neurons and repression of the MAPK/ERK pathway.

Isomescaline (IM), also known as 2,3,4-trimethoxyphenethylamine (2,3,4-TMPEA) or as TMPEA-3 or 2C-TMA-3, is a chemical compound of the phenethylamine and scaline families related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine; 2,3,4-TMPEA). It is one of several possible positional isomers of trimethoxyphenethylamine (TMPEA). In addition, it is the positional isomer of mescaline in which the methoxy groups on the phenyl ring are located at the 2, 3, and 4 positions instead of at the 3, 4, and 5 positions.

Tiapamil (INN; also known as dimeditiapramine) is a calcium antagonist or calcium channel blocker. It is an experimental drug that has never been marketed.

Lophophine, also known as 2C-MMDA-1, 5-methoxy-MDPEA, or 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA or MMDPEA-1), is a psychedelic drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline (3,4,5-trimethoxyphenethylamine) and MDPEA. Lophophine has been encountered as a novel designer drug.

2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a serotonin receptor modulator of the phenethylamine and 2C families related to the psychedelic drug mescaline. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue of 2,4,5-trimethoxyamphetamine (TMA-2). The drug is the parent compound of the 2C-O series of drugs. 2C-O appears to be inactive in terms of psychoactive effects in humans, at least at doses that have been assessed. In any case, it is a low-potency full agonist of the serotonin 5-HT2 receptors in vitro,

psychedelic

chemical compound

MEDA, also known as 3-methoxy-4,5-ethylenedioxyamphetamine or as 5-methoxy-EDA, is a chemical compound of the phenethylamine, amphetamine, and EDxx families. It is the EDxx analogue of the MDxx psychedelic and entactogen MMDA (5-methoxy-MDA). In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MEDA's dose as greater than 200mg orally and its duration as unknown. MEDA produced few to no effects at tested doses. The chemical synthesis of MEDA has been described. MEDA was first described in the scientific literature by Shulgin in 1964. Subsequently, it was describ

Ibopamine is a sympathomimetic drug, designed as a prodrug of epinine (deoxyepinephrine or N-methyldopamine), used in ophthalmology. It induces mydriasis. It also has been investigated for use in the treatment of congestive heart failure.

chemical compound

chemical compound

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA or DMMDA-1) is a lesser-known psychedelic drug of the amphetamine and MDxx families related to MMDA. It was first synthesized by Alexander Shulgin in the 1960s and was described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

DMMDA-2, also known as 2,3-dimethoxy-4,5-methylenedioxyamphetamine or as 5,6-dimethoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA. It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.

MEPEA, also known as 3-methoxy-4-ethoxyphenethylamine or as 3-desmethoxyescaline, is a psychoactive drug of the phenethylamine family related to the psychedelic drug mescaline. It is the analogue of escaline in which the methoxy group at the 5 position has been removed.

'''para-Methoxyethylamphetamine (PMEA''') is a stimulant drug related to PMA. PMEA reputedly produces similar effects to PMA, but is considerably less potent and seems to have slightly less tendency to produce severe hyperthermia, at least at low doses. At higher doses however the side effects and danger of death approach those of PMA itself, and PMEA should still be considered a potentially dangerous drug. Investigation of a drug-related death in Japan in 2005 showed PMEA to be present in the body and was thought to be responsible for the death.

chemical compound

Meta-DOB, also known as 5-bromo-2,4-dimethoxyamphetamine, is a psychoactive drug of the phenethylamine and amphetamine families related to the psychedelic drug DOB. It is a positional isomer of DOB in which the bromine atom at the 4 position and the methoxy group at the 5 position have been interchanged.

'''para-Ethoxyamphetamine (PEtOA), also known as 4-ethoxyamphetamine (4-EA, 4-ETA, or 4-EtO-A'), is a psychoactive drug of the phenethylamine and amphetamine families which is closely related to para''-methoxyamphetamine (PMA). It has similar effects to PMA in animal studies, although with slightly weaker stimulant effects. Like PMA, it has prominent MAOI activity, and is likely to have similar dangers associated with its use.

1-Aminomethyl-5-methoxyindane (AMMI), is a drug developed by a team led by David E. Nichols at Purdue University, which acts as a selective serotonin releasing agent (SSRA) and binds to the serotonin transporter (SERT) with similar affinity relative to DFMDA.

Meta-DOT, also known as 5-methylthio-2,4-dimethoxyamphetamine or as 5-thio-TMA-2, is a psychoactive drug of the phenethylamine and amphetamine families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with a methylthio group. In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).

chemical compound

UH-232 ((+)-UH232) is a drug which acts as a subtype selective mixed agonist-antagonist for dopamine receptors, acting as a weak partial agonist at the D3 subtype, and an antagonist at D2Sh autoreceptors on dopaminergic nerve terminals. It causes dopamine release in the brain and has a stimulant effect, as well as blocking the behavioural effects of cocaine. It may also serve as a 5-HT2A receptor agonist, based on animal studies. It was investigated in clinical trials for the treatment of schizophrenia, but unexpectedly caused symptoms to become worse.

MEAI, also known as 5-methoxy-2-aminoindane (5-MeO-AI) and by its developmental code name CMND-100, is an entactogen-like psychoactive drug of the 2-aminoindane family. It is a cyclized phenethylamine and is the 2-aminoindane analogue of 3-methoxyamphetamine. The drug acts as a serotonin–norepinephrine releasing agent (SNRA) or as a modestly selective serotonin releasing agent (SSRA), with about 6-fold preference for induction of serotonin over norepinephrine release. MEAI has been encountered as a novel designer recreational drug. It is also under development for potential medical use in the

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.

3-Methoxyamphetamine (3-MA), also known as '''meta-methoxyamphetamine (MMA'), is a monoamine releasing agent (MRA) of the amphetamine family. It is a positional isomer of para''-methoxyamphetamine (PMA; 4-methoxyamphetamine). The drug has been encountered as a novel designer drug.

3-Methoxymethamphetamine (also known as '''meta-methoxymethamphetamine or MMMA'''), which is most closely related to 3-methoxyamphetamine and PMMA and shares similar monoamine releasing effects, although its effects have not been studied so extensively as other related drugs.

PNU-99,194(A) (or U-99,194(A)) is a drug of the 2-aminoindane family which acts as a moderately selective D3 receptor antagonist with ~15-30-fold preference for D3 over the D2 subtype. Though it has substantially greater preference for D3 over D2, the latter receptor does still play some role in its effects, as evidenced by the fact that PNU-99,194 weakly stimulates both prolactin secretion and striatal dopamine synthesis, actions it does not share with the more selective (100-fold) D3 receptor antagonists S-14,297 and GR-103,691.

RDS-127, also known as '4,7-dimethoxy-N,N-dipropyl-2-aminoindane', is a drug of the 2-aminoindane family which is used in scientific research. It acts as a D2-like receptor agonist and also has some serotonin and adrenergic agonist effects, as well as some anticholinergic action, and produces both anorectic and pro-sexual effects in animal studies.

chemical compound

Devapamil is a calcium channel blocker. It is also known as desmethoxyverapamil, which is a phenylalkylamine (PAA) derivative. Devapamil not only inhibits by blocking the calcium gated channels, but also by depolarizing the membrane during the sodium-potassium exchanges.