2C-I (4-iodo-2,5-dimethoxyphenethylamine) is a psychedelic phenethylamine first described by chemist Alexander Shulgin in his book PiHKAL: A Chemical Love Story. 2C-I is usually taken orally or insufflated with a typical dose in the range of 10-20mg. 2C-I has both hallucinogenic and entactogenic properties, and is often described as being more physically stimulating than other phenethylamines. The major effects of the drug at a typical dose last for approximately 4-6 hours.
Introduction to 2C-I
2C-I (2,5-dimethoxy-4-iodophenethylamine), part of a series of analogues informally referred to as the '2Cs', is a methoxylated phenethylamine derivative. It is distinguishable from other members of the '2C' series due to an iodine substituent para to the ethylamine chain.
Ways of administrationOral, insufflation, rectal, I.V.
Effects of 2C-I
Combinations with 2C-I
Different Uses for 2C-I
Pharmacology of 2C-I2C-I inhibits the reuptake of monoamines, which include dopamine, norepinephrine, and serotonin - though exerts its predominant inhibition on serotonin and norepinephrine. In comparison to other members of the '2C' series of methoxylated phenethylamine derivatives, Nagai et. al. observed that 2C-I is slightly less potent at inhibiting serotonin reuptake than 2C-E and 2C-C, but more potent than both 2C-E and 2C-C at inhibiting reuptake of norepinephrine. No members of the methoxylated phenethylamines (including the '2Cs' and TMAs) were significantly active as inhibitors of dopamine re-uptake.
When evaluated for its capacity to stimulate monoamine release, 2C-I (as well as 2C-E and 2C-C) was characterized by relatively low levels of activity as compared to other phenethylamines such as MDMA, Methylone and MBDB.
Comparison of re-uptake inhibition to other phenethylaminesIn comparison to other phenethylamines, 2C-I (as with other members of the '2C' series) appears to more potently inhibit the reuptake of both serotonin and norepinephrine than TMA, TMA-2, and TMA-6. 2C-I is a less potent re-uptake inhibitor, however, of both serotonin and norepinephrine than MDMA, Methylone, MBDB, and BDB (Benzodioxolylbutanamine).
Comparison of re-uptake inhibition to selected tryptaminesWhen compared to the tryptamines, the methoxylated phenethylamines - which include members of the '2C' series as well as the 'TMA' series - exhibit lower IC50 values, rendering them less active as re-uptake inhibitors. Specifically, Nagai et. al. observed that AMT (and it's 5-MeO analogue), DPT, 5-MeO-DIPT, 5-MeO-MIPT, and 5-MeO-DMT all exhibited greater inhibition of reuptake for both serotonin and norepinephrine.
Effects on monoamine re-uptake into rat brain synaptosomeBelow is a table taken from Nagai et. al., 2006 that includes 2C-I in comparison to other Phenethylamines, tryptamines, and piperazines - including cocaine and methamphetamine.
In relation to other phenethylamines, the methoxy analogues (including 2C-I, 2C-E, 2C-C, TMA, TMA-2, and TMA-6), exert comparatively weaker effects on reuptake and release of monoamines. However, Nagai et. al. are careful to suggest that the drugs may present post-synaptic effects that are unaccounted for.
Studies of Cortical G-Protein BindingNonaka et. al. assessed the potency of several Phenethylamines, tryptamines and piperazines by assessing GTP-binding, in concentration-dependent manners, to cortical membranes. Below is a concentration curve for [35S]GTPgS cortical binding by several drugs, including 2C-I in (A).
The curves demonstrate that, of the tested drugs considered members of the '2C' series, 2C-I bound to G-Protein coupled receptors more potently than 2C-E, but less potently than 2C-C.
In comparing 2C-C, 2C-I, and 2C-E - the only difference in structure concerns the substituent present at the 4-position of the aromatic ring (chloride, iodide, and ethyl, respectively). Nonaka et. al. propose that, from order of potency, a steric hindrance similar to that of the 5-MeO-tryptamines exists. They cite Glennon et. al. as suggesting that behavioral activity of phenethylamine drugs depend upon the size of the substituent at the 4-position of 2,5-di-methoxyamphetamine as a parent structure; the results of the above experiment suggest that steric hindrance is crucial in the binding of compounds to serotonin receptors.
In other words, potency at serotonin receptors is likely restricted by the size of the group bound at the 4-position - in this case, iodine - which is a larger atom than chloride but sterically smaller than an ethyl group. Accordingly, 2C-B would be anticipated to be more potent than 2C-I and slightly less potent than 2C-C.
Chemistry of 2C-I
See: 2C-I solubility in water and Solubility of 2C-E & 2c-i.
Column 1 Column 2 Systematic (IUPAC) name: 4-iodo-2,5-dimethoxybenzeneethanamine Synonyms: 4-iodo-2,5-dimethoxyphenetylamine Molecular Formula: C10H14INO2, C10H14INO2.HCl (hydrochloride) Molar mass: 307.13 g/mol, 343.59 g/mol (Hydrochloride) CAS Registry Number: 69587-11-7 (hydrochloride) Melting Point: 248-250°C (hydrochloride)  Boiling Point: no data Flash Point: no data Solubility: Hydrochloride very soluble in methanol, water; soluble in chloroform, ether; sparingly soluble in acetone Additionnal data: none Notes: none
Reagent test results of 2C-I
Reagent color produced picture video Marquis Green, blue link (reference); link (results) - Mandelin Reddish brown link (reference); link (results) - Mecke Biege, brown black link (reference); link (results) -
The dangers of 2C-IThese are the dangers common to all psychedelic drugs:
Accidental injury. When on a psychedelic drug, it is easier to accidentally injure yourself. Also because of the disorientating and potentially delusion inspiring nature of the experience, you could be lead to inflict harm on others or yourself. People have fallen off rooftops, run into traffic, attempted to throw people off rooftops as 'sacrifices', drowned, and so on. The best way of protecting against this is to have a friend with you who is sober to look after you and handle any negative situation that might arise.
Bad trips. A bad trip is a negative psychedelic experience. It can range from a mildly negative feeling of anxiety/discomfort, to full-blown psychosis. Bad trips usually ruin a psychedelic experience for the tripper and everyone else. Most bad trips are manageable, just very uncomfortable and difficult. Some are extreme and unmanageable though. It's not uncommon for a bad trip to result in lingering psychological issues. Usually just a few days of negative emotions and anxiety. Sometimes, however, a week or so of serious anxiety, destabilized mental state and impaired functioning is possible. On very rare occasions, a month or two of severely diminished functioning, traumatized mental state, depression & crippling anxiety can occur. More information on bad trips can be found here. The best way of avoiding a bad trip is having the correct set and setting.
Permanent psychosis. Psychedelics are believed by researchers not to cause permanent psychosis, however they could trigger a latent mental illness in someone who was already predisposed to it, or make existing mental illnesses worse. If there is a history of mental illness in your family, you are more likely to be predisposed. Everyone is at some risk, however.
PTSD, anxiety disorder, depression & depersonalization. There are anecdotal reports of the trauma inflicted by some bad trips leading to depression and anxiety which while usually temporary, could potentially develop into lasting disorders. While no different to the potential of any traumatic event to cause lasting disorders, nonetheless this is a danger of psychedelic drug use.
Forms of 2C-I
Legal status of 2C-I
2C-I is a controlled substance.
USA2C-I is not explicitly controlled at Federal level, though possession or distribution may under certain circumstances contravene the Federal Analog Act due to 2C-I's structural and functional similarity to the Schedule I controlled substance 2C-B.
United Kingdom2C-I is a class A controlled substance as it is covered by the phenethylamine derivatives clause of the Misuse of Drugs Act 1971.
FinlandIllegal since 2011 
History of 2C-I
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The latest 2C-I threads
- ^ a b cNagai, Fumiko, Nonaka, Ryouichi, Satoh, Kanako, Kamimura, Hisashi, The eﬀects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain, European Journal of Pharmacology (2006)
- ^ a bNonaka, Ryouichi, Nagai, Fumiko, Akio, Ogata, Satoh, Kanako, In Vitro Screening of Psychoactive Drugs by [35S]GTPgS Binding in Rat Brain Membranes (2007)
- ^Calculated from Atomic Weights of the Elements, 2007
- ^ a b c d
- ^http://www.finlex.fi/fi/laki/ajantasa/2008/20080543 Categories: 2C-x Chemical Family, Hallucinogens, Phenethylamines, Psychedelics, Research Chemicals