2C-I

2C-I

Names
IUPAC name 2,5-Dimethoxy-4-iodophenethylamine
Identifiers
CAS Number	69587-11-7 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL338297 Y
ChemSpider	8442670 Y
ECHA InfoCard	100.217.507
PubChem CID	10267191
CompTox Dashboard (EPA)	DTXSID80893674
InChI InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 Y Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N Y InChI=1/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 Key: PQHQBRJAAZQXHL-UHFFFAOYAK
SMILES Ic1cc(OC)c(cc1OC)CCN
Properties
Chemical formula	C10H14INO2
Molar mass	307.13 g/mol
Melting point	246 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. It was described in Shulgin’s book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects. 2C-I is commonly sold in its hydrochloride salt form, which is a fluffy, sparkling-white powder, which has also been pressed into tablet form.

Recreational use

In the early 2000s (decade), 2C-I, was sold in Dutch smart shops, after 2C-B, which was previously sold, was banned. In April 2008, 2C-I was also banned in the Netherlands, along with three other 2C-x phenethylamines previously sold in Dutch smartshops for short periods of time. During the same period, 2C-I also became available in powder form from several online vendors of research chemicals in the United States, Asia, and Western Europe.

It is often misrepresented as mescaline in US street sale of singular dosages, as it shares some level of similarity in psychological effect. Both chemicals are members of the psychedelic phenethylamine class of drugs, except 2C-I is an analog of mescaline in the 2C-x series. A major difference between the research chemicals in the 2C-x series and mescaline is a much greater potency by weight and thus also a steeper dose-response in the newer synthetic drugs. 2C-I's effective dosage range per milligram is approximately 10-fold less than mescaline. This means that a small carrier material, such as a small candy or pressed pill, is suitable for 2C-I. That type of small carrier material has an insufficiently small holding capacity to contain a large enough quantity of mescaline to produce a substantial psychoactive effect. In addition, mescaline sounds inherently less dangerous to consume to the lay-man rather than a relatively obscure compound of modern innovation with less documentation of potential long-term effects in humans. 2C-I also lacks the history of natural use as a ethnobotanical in the spiritual traditions of some cultures, unlike the peyote from which mescaline is derived.

2C-I is usually taken orally. It can also be administered rectally or insufflated, though 2C-I often causes considerable pain upon insufflation. It is also possible to smoke or vaporize it, although the dose required is higher. There have also been a few reports of intramuscular and intravenous injections. Intravenous doses should not be self-administered due to the immediate onset of hallucinations and strong physical stimulation before the needle's plunger is fully depressed. An oral recreational dose of 2C-I is commonly between 10 mg and 25 mg, although doses as low as 2 mg have been reported to be active.

Effects

The onset of effects usually occurs within two hours, and the effects of the drug typically last somewhere in the range of 4 to 12 hours (depending on the dose). The effects of the drug at small dosages (less than 12 mg) has been reported as more mental and less sensory than those of 2C-B. Users of 2C-I do, however, tend to report a physical stimulant effect, often quite strong and clean. The effects of the drug at larger dosages (12-30+ mg) are often described as combining psychedelic or hallucinogenic effects typical of drugs such as LSD with the empathogenic or entactogenic effects of drugs such as MDMA (ecstasy). Although unpleasant physical side-effects such as muscle tension, nausea, and vomiting have been reported, their incidence with the use of 2C-I appears to be less common than with some closely related phenethylamines such as 2C-T-2 and 2C-T-7. Some physical effects include dilated pupils, high energy, and muscle relaxation. Users report feeling light and sometimes giddy or excited during the first two hours. Users also report that heavy music, usually electronic, and other auditory stimulation is enjoyable.

Dosage

Oral Dosage
ED50	2–5 mg
light	5–10 mg
Common	10–20 mg
Strong	20–30 mg
LD50	Unknown
Duration	4-12 Hours
Insufflated (Snorted) Dosage
ED50	0.5–2 mg
Moderate	5–10 mg
Strong	10+ mg
Duration	4-8 Hours

The lethal dosage is unknown.

Side-effects

2C-I tablet

Large doses of 2C-I (>45 mg), like other phenethylamines, may result in undesirable psychological effects, the persistence and severity of which are largely undocumented. Multiple deaths in 2012 have been attributed to the drug along with seizures, kidney failure and fatally high blood pressure.

Law

As of July 9, 2012, in the United States 2C-I is a Schedule I substance under the Synthetic Drug Abuse Prevention Act of 2012, making possession, distribution and manufacture illegal.

2C-I is an illegal, controlled substance in several European nations, including Denmark, Germany, Greece, Ireland, Italy, the Netherlands, Poland, Spain, and the United Kingdom. In December 2003, the European Council issued a binding order compelling all EU member states to ban 2C-I within three months.

Usage

The drug has seen a rise in use 2012, and is suspected to be a factor in the death of actor Johnny Lewis. The drug has also been implicated in several other deaths nationwide.

See also

• Empathogen-entactogen
• Phenethylamine
• Psychedelic
• Recreational drug use
• Alexander Shulgin
• 2C family

External links

• Erowid 2C-I Vault
• 2C-I Entry in PiHKAL
• 2C-I Entry in PiHKAL • info