Clinical data | |
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Other names | 2-Indanylamine; 2-Indanamine |
Routes of administration | Oral |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.019.111 |
Chemical and physical data | |
Formula | C9H11N |
Molar mass | 133.194 g·mol−1 |
3D model (JSmol) | |
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2-Aminoindane (2-AI) is an aminoindane and research chemical with applications in neurologic disorders and psychotherapy that has also been sold as a designer drug. [1] It acts as a selective substrate for NET and DAT. [2] [3]
Synthetic aminoindanes were originally developed in the context of anti-Parkinsonian drugs as a metabolite of rasagiline and as a tool to be used in psychotherapy. Deaths related to their toxic effects have been observed both in the laboratory in animal studies and in clinical encounters. [4]
2-AI is a rigid analogue of amphetamine and partially substitutes for it in rat drug discrimination tests. [5] [6] Other related homologues and rigid analogues of amphetamine include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronapthalene (2-ADN), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), 6-AB , and 7-AB . [6] [5] [7]
There are a number of notable derivatives of 2-aminoindane that exist, including:
A number of notable derivatives of 1-aminoindan, a positional isomer of 2-aminoindan, also exist, such as rasagiline and ladostigil, among others.
Jimscaline, 2CB-Ind, and AMMI are derivatives of 1-aminomethylindane, an indane- and amine-containing compound related to 1-aminoindan.
Compound | Monoamine release (EC50 , nM) | ||
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Serotonin | Norepinephrine | Dopamine | |
2-AI | >10000 | 86 | 439 |
MDAI | 114 | 117 | 1334 |
MMAI | 31 | 3101 | >10000 |
MEAI | 134 | 861 | 2646 |
Notes: The smaller the value, the more strongly the compound produces the effect. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. |
As of October 2015 2-AI is a controlled substance in China. [9]
Scheduled in the "Government decree on psychoactive substances banned from the consumer market". [10]
Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019. [11]
2-Aminoindane is not scheduled at the federal level in the United States, [12] but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.
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.
4-Fluoroamphetamine, 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. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine.
Rasagiline, sold under the brand name Azilect among others, is a medication which is used in the treatment of Parkinson's disease. It is used as a monotherapy to treat symptoms in early Parkinson's disease or as an adjunct therapy in more advanced cases. The drug is taken by mouth.
Naphthylaminopropane, also known as naphthylisopropylamine (NIPA), is an experimental drug that was under investigation for the treatment of alcohol and stimulant addiction.
MEAI, also known as 5-methoxy-2-aminoindane (5-MeO-AI), is a monoamine releasing agent of the 2-aminoindane group. It specifically acts as a selective serotonin releasing agent (SSRA). The drug is under development for the treatment of alcoholism, cocaine use disorder, metabolic syndrome, and obesity under the developmental code name CMND-100.
MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.
A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters.
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.
5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug of the 2-aminoindane group developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a less neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogenic effects in humans. It has been sold as a designer drug and research chemical online since 2010.
5-Iodo-2-aminoindane (5-IAI) is an entactogen drug of the 2-aminoindane group. Human anecdotal reports suggest that it is entactogenic but produces little euphoria or stimulation.
Aminoindane refers to a class of compounds that are structurally related to indane, a bicyclic hydrocarbon. These compounds are characterized by the presence of an amino group attached to the indane structure. Aminoindanes have been studied for their potential applications in various fields, including medicine and neuroscience.
2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug with a chemical structure consisting of a tetralin group combined with an amine.
3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.
2-Amino-1,2-dihydronapthalene is a stimulant drug. It is a rigid analogue of phenylisobutylamine and substitutes for amphetamine in rat drug discrimination tests, although at approximately one-fourth the potency.
3,4-dichloromethylphenidate is a potent stimulant drug from the phenidate class closely related to methylphenidate. It acts as a potent serotonin-norepinephrine-dopamine reuptake inhibitor with a long duration of action. It has been sold online as a designer drug.
1-Phenylpiperazine is a simple chemical compound and drug featuring a phenyl group bound to a piperazine ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.
The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.
(R)-1-Aminoindan ((R)-1-AI; developmental code name TVP-136 or TV-136), or (R)-1-aminoindane, is the major metabolite of the selective MAO-B inhibitor and antiparkinsonian agent rasagiline ((R)-N-propargyl-1-aminoindan). In contrast to rasagiline, it lacks significant monoamine oxidase inhibition. In addition, unlike selegiline and its amphetamine metabolites, it lacks monoamine reuptake-inhibiting and -releasing activities and associated amphetamine-like psychostimulant effects. However, (R)-1-aminoindan retains neuroprotective effects and certain other activities.
1-Aminoindane (1-AI), also known as 1-aminoindan, 1-indanylamine, or 1-indanamine, is an aminoindane. It is a positional isomer of 2-aminoindane. A variety of notable derivatives of 1- and 2-aminoindane are known. The (R)-enantiomer of 1-aminoindan, (R)-1-aminoindan, is pharmacologically active and is an active metabolite of the antiparkinsonian agent rasagiline.
The Borax combo, also known by the informal brand names Blue Bliss and Pink Star, is a combination recreational and designer drug described as an MDMA-like entactogen.