2C2-NBOMe
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2C2-NBOMe, also known as 2C-MMDA-2-NBOMe or NBOMe-MMDPEA-2, is a
phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
from the
25-NB The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. The most commonly encountere ...
(NBOMe) family. It is the NBOMe
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
of 2C-MMDA-2 (MMDPEA-2). It acts as a potent
agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...
at the
serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
5-HT2A
receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...
with weaker activity at 5-HT2B and 5-HT2C, and produces a
head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...
in animal studies which often correlates with potential for
psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
effects in humans. It is related in structure to psychedelic phenethylamine derivatives such as
MMDA-2 MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA. Alexander Shulgin was likely the first to synthesize MMDA-2. In his book ...
and
lophophine Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related t ...
(MMDPEA) and is the first phenethylamine derivative with a
methylenedioxy Methylenedioxy is the term used in the field of chemistry, particularly in organic chemistry, for a functional group with the structural formula which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consist ...
substitution on the phenyl ring but no alkyl substitution on the alpha carbon, that has been shown to produce psychedelic-appropriate responding in animals. The drug was first described in the literature by
Jason Wallach Jason Wallach (born 1987) is an American pharmacologist who studies psychedelic drugs and other hallucinogens. He is an assistant professor at Saint Joseph's University's Philadelphia College of Pharmacy. In August 2020, Wallach began a partners ...
and colleagues in 2022 and 2023.


See also

*
Substituted methoxyphenethylamine Methoxyphenethylamines (MPEAs), as well as methoxyamphetamines (MAs) in the case of the amphetamine (α-methylphenethylamine) homologues, are substituted phenethylamines with one or more methoxy groups. In some cases, one or more of the methoxy ...
*
25-NB The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. The most commonly encountere ...
*
25C-NBOMe 25C-NBOMe, also known as NBOMe-2C-C, 2C-C-NBOMe, or Cimbi-82, is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. It acts as a potent agonist of the 5-HT2A receptor, and has been studied in its 11C radiolabelled form a ...
(NBOMe-2C-C) *
DMMDA 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA or DMMDA-1) is a lesser-known psychedelic drug of the amphetamine family related to MMDA. It was first synthesized by Alexander Shulgin in the 1960s and was described in his 1991 book ''PiHKAL ...
*
MMDA (drug) MMDA, also known as 3-methoxy-4,5-methylenedioxyamphetamine or as 5-methoxy-MDA, is a psychedelic and entactogen of the amphetamine family. Use and effects MMDA was described by Alexander Shulgin in his book ''PiHKAL''. Shulgin lists the dosage ...
*
MDPEA 3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to MDA, but without the methyl gro ...
*
NBOMe-mescaline NBOMe-mescaline, also known as mescaline-NBOMe, M-NBOMe, or ''N''-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine, is a serotonin receptor agonist and putative psychedelic drug of the phenethylamine, scaline, and ''N''-benzylphenethylamine (N ...


References


External links


2C-MMDA-2-NBOMe - Isomer Design
2-Methoxyphenyl compounds 25-NB (psychedelics) 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists Methoxyphenethylamines Methylenedioxyphenethylamines Psychedelic phenethylamines {{Hallucinogen-stub