Citation: Glarble. "Happy That I Started Small: An Experience with 2C-I (exp110711)". Erowid.org. Sep 28, 2017. erowid.org/exp/110711
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2C-I Synthesis and First Two Experiences
[Preparation details below experience description]
Background: I am fairly well experienced with drugs of various classes, and have had multiple experiences with mushrooms, LSD, 2C-B, DMT, cocaine, various opiates/opioids, and have been a near-daily user of marijuana for about 12 years. I also drink beer fairly regularly. In the following experiences I began while completely sober. I had probably drank a few beers the nights previous to the experiences.
Trial 1: 10.5 mg, 27 Nov 2015
For my first trial, I decided to try 10.5 mg while I was alone at home, sick with a cold/respiratory infection. Despite the illness, I was relatively comfortable at home, and in good spirits. About an hour prior to ingestion I had eaten a light breakfast consisting of one egg, one slice of wheat toast with butter and two cups of coffee with half and half. At 10:23 am (T+[0:00]) I ingested the dose with Emergen-C and water. The plain 2C-I powder has a strange sweetish bitter taste.
I watched one episode of Naruto, then got into the shower at [0:22]. The following is copied from my handwritten notes taken during the experience, with additional comments in parentheses.
[0:48] Possible first alerts (Tightness in stomach, a change in light and color noticed)
[1:10] (+) Typical phenethylamine visuals (“Persian carpet” type, growing and twisting vines, light and shadow moving back and forth much like gentle waves on a beach). Mild, subtle. Listen to Acheron/Unleashing the Orb, Tres Brujas (by The Sword), Orbital Elements (by Obscura). The music sounded more clear and enjoyable than usual. I could see the bands playing in my mind’s eye, and could see everything they were playing and how they played it. I believe after listening to Orbital Elements I decided to listen to the entire album, “Cosmogenesis,” though I may have waited an hour or two to do this. (Can’t remember for sure.)
[2:15] Perhaps (++) now, visuals a little more pronounced, still subtle. Feel warm, temperature normal.
[3:00] Still about (++). This may be the peak. Nice, warm, gentle. Smoke some pot (one or two hits). Interesting modification – some intensification. I lied back and stared at the textured ceiling, and began to see in it letters and words. In three-dimensional block letters, there manifested the word “BUMMERFEST,” with a hand giving the middle finger coming out of the top of the first “M.” I found this highly amusing and decided to draw it in my notes with an arrow pointing to the “bummerfest” drawing: 'see this in the ceiling, among other things. Not bummed.'
[3:15] At this point I was definitely listening to either “Cosmogenesis” or “Omnivium” by Obscura, a highly technical and pretty dang psychedelic metal band. The music is so technical that it is a little difficult to follow when sober, but with 2C-I I feel as though I can hear every note of every instrument, as well as subtle sounds and effects I don’t usually notice. I took no notes at this point, but instead decided to draw and doodle with my pencil, making marks to the sound of the music. I first drew what appears to be a scene with scroll/wavy sheet of paper with squiggles for writing rising from a sea, framed by spiral-y clouds and seaweed beneath.
[3:30] I started drawing what was starting to look like four people in hazmat suits standing side by side, but these became the fingernails of a hand with fingers held together, tapping on a surface and surrounded by wavy flame-like shapes. I then drew a very abstract something or other, vaguely television-shaped, containing perhaps reeds, with an abstract representation of the sun (?) and perhaps a bird or tea kettle-like thing. I write: more proper psychedelic state – may have been the weed. I think at this point I tried to draw the sound, and made another very abstract image, consisting of strata with trapezoidal corrugated tin roofing shapes, the bottom layer pulled out from the ones above. Beneath this are circles/spheres, spirals and speckles. I finish drawing at T+[3:44]
[3:44] Obscura is exquisite
[4:15] Obscura still awesome. Maybe (++ ½). Probably should eat should eat something. Ate food.
[5:17] Having chai, probably coming down now.
After this, I think I just smoked more pot and relaxed for the rest of the day. I don’t remember experiencing any ill effects/hangover, however two days later I tried 18.8 mg of 2C-B hydrobromide – the highest dose I had yet tried – and had an experience on about the same level as my previous experiment with 14 mg. So there may have been a bit of tolerance induced by the 2C-I.
Trial 2: 14 mg, 31 Dec 2016
At 7:51 am (T –[0:55]) I finish food, coffee (2 bacon, 2 eggs, 1 slice toast + butter, 2 coffee + half and half)
8:06 am I smoke some pot, one or two hits
8:46 am (T[0:00]) Ingest 14 mg 2C-I hydrochloride in water, rinsing the glass twice with small amounts of water and drinking to ensure the entire dose was taken.
[0:04] I get my boots and jacket on, go outside to shovel snow and check the propane level in the tank. It is ~4° F outside.
[0:12] I return, remove outside clothes and play guitar for a few minutes to pass the time
[0:36] Out and dressed, nothing yet
[0:47] First alert, perhaps – feel in in my stomach, slight head stimulation, color awareness (watching One Piece).
[1:00] Some more stomach “tightness” (vasoconstriction?), bit of a head buzz, some warmth felt in genitals. Colors more noticeable, “soft.” I could really see the color of my curtains. The green from the southwest curtain – yellow flowers and green leaves/stems on white – seemed to project onto the ceiling above it. Same with the orange from the orange-brown west curtain.
[1:10] ~(+) Pupils beginning to dilate, no visuals yet. Shaky, “stoned” feeling similar to 2C-B come-up. Guitar for a couple minutes, then watch the young deer through the window eat pine for a couple minutes.
[1:20] Feeling spacey. Some slight visual distortion in I relax/focus.
[1:30] Perhaps (++). Visual phenomena only when I look for it/them.
[1:32] (Almost immediately after writing the above) Textured wall beginning to resemble cursive writing – Glassy, Gravy, Hippy, etc. Crawling/scrunching movements, typical of mescaline, 2C-B
[1:42] Effects real but mild. Put on Obscura album “Akróasis,” smoke some pot (one hit). Obscura is highly enjoyable on 2C-I. They complement each other beautifully. I feel as though I am capable of hearing “more” in this state. Still don’t understand (most) vocals. Just music.
[1:58] Developing pleasantly, pot may have augmented. Paisley patterns and eyes in fireplace/mantle. Music and visual patterns seem to go together. I seem to forget to put a letter in some words while writing.
[2:03] This album not so good after 4-5 songs…
[2:12] …Was going to switch, then my girlfriend R came home from work for her ten minute break. Feeling stronger, had a surge of “too much?” anxiety, but still in control. Probably safe to call this (+++) now. Pupils ~50% dilated. The effects had been pretty mild until R got home. She knew what was going on and was okay with it, but my mind started racing as I wondered how I should be behaving, what should I say if anything at all. I suddenly realized that I was quite high, my pulse was increasing and I wanted to breathe more/faster. I breathed deeply a few times, told myself I was fine and to relax. I sat back and listened to myself and my heart calmed down, as did my breathing. After R left I was collected enough to write the above.
[2:18] Put on “Omnivium.”
[2:40] Have been mostly in reverie. Seeing faces/skulls/masks (in the light and shadows on the ceiling). Lost in thought/visuals.
[2:58] Pretty well smoothed out. Been trying to decide whether to smoke more pot or not. Visuals fairly consistent/persistent. Keep finding myself spaced out “half-thinking” about this or that, nothing in particular.
[3:10] Smoked a little more pot. Noticed some details of non-cleanliness in kitchen (it looked FILTHY) earlier probably would have passed over otherwise (i.e. sober).
[3:13] Feel a little “tooth-rubby.”
[3:16] “Concerto” is such a “sweet” ending to Omnivium, like a nice little after-dinner mint to top off the weird but exquisite 9-course meal that was the rest of the album.
[3:19] Another hit of pot.
[3:30] Everything (outside) looks as if dusted in sugar – all is frosted over from freezing fog. Quite beautiful, very bright. Hearing heightened. Listen to birds at neighbor’s feeder.
[3:37] Heard people across the street as if they were right outside door. Had to check.
[3:45] (+++) Trippy. Feels as though everything is painted (like a painting). Some parallels between these visuals and those of DMT (esp. last experience). Geometric/fractal, many colors/contrasts.
[3:49] Visions – landscapes, strange geometric textures, wire structures, fine filigree.
[4:10] Cleaned kitchen a bit, still moderate (+++). Ate some Swedish-style wortlimpa, hung out with R on her lunch break. I was peaking before and during R’s arrival, but while she was home I felt the need to try to be capable of communicating if need be so I tried to tamp back my mind-state.
[5:00] Maybe waning, now? Perhaps (++). Some physical side effects noted – tightness in jack (I meant jaw) and neck. Slight headache.
[5:10] Another hit of weed.
[5:20] Lay back – interesting CEV – kaleidoscopic. Also surrealistic cartoonish scenery.
[5:34] Staring at the Owl Picture, leaves sway in breeze. (I keep feeling as though I am coming down, and wonder if maybe now might be an okay/interesting time to try a little DMT. Several times, as I think about maybe smoking some DMT, the leaves and branches in the large owl painting move and flap in non-existent wind, sometimes spinning to form a ring.)
[5:40] Orbital Elements, other metal instrumentals
[6:00] Not sure what to make of this. Somewhere between (++) and (+++). Venture outside.
[6:12] Back. Cold out there (~15° F). Everything seems clean, crisp outside.
[6:17] Decide to smoke DMT residue – nothing much there. Search for screens, load 4 into pipe.
[6:32] Vaporize DMT from 7/2014 (weighed and kept in the freezer), 12 mg
[6:38] Wow/crap/damn haha - Hit hard (though not quite “break-through”), amazing visuals – Aztec/space alien designs and a very uncomfortable feeling – don’t want to here/not allowed to be here – unreal. Was worried for a difficult ~4 seconds that this intense weirdness would persist for several hours but effects quickly diminished, allowing this writing.
[6:50] Completely down from DMT, 2C-I effects seem to be dropping more. Smoke weed, eat.
[7:14] Stoned from weed, ~(+) from 2C-I.
Overall, I find 2C-I to be an interesting drug, though not my personal favorite. I think I prefer 2C-B, which seems to produce a softer, more soulful experience that I find to be more generally pleasant. 2C-I seems to produce a more decidedly intellectual trip, which has value in its own right. Appreciation for complex music is increased, and if a good friend or two were present to share the experience good intellectual conversation would almost surely be had.
Under other circumstances, like if I had someone to trip with, I might up the dosage to 15 or 16 mg, but for me at this time 14 was just right. 2C-I is clearly more potent than 2C-B on both a molar and mass basis and the common dosage of 20 mg seems, after these experiences, to be far too much for someone of my size. I am incredibly happy that I started small and worked my way up with dosage.
2,5-dimethoxynitrostyrene was prepared in several steps, starting from hydroquinone. The following preparation of the nitrostyrene from hydroquinone is just a summary, as all of these procedures are available around the internet. Hydroquinone was converted to 4-methoxyphenol by stirring at room temperature in methanol with catalytic sulfuric acid and benzoquinone for 24 hours, neutralizing the acid with equimolar sodium bicarbonate, filtering, and vacuum distillation of the product. 4-methoxyphenol was formylated to 2-hydroxy-5-methoxybenzaldehyde using magnesium methoxide and paraformaldehyde in toluene, the product isolated by acidification of the magnesium salt, removal of the solvent and vacuum distillation of the product. The phenolic benzaldehyde was converted to the potassium salt by KOH in ethanol, filtered, and methylated by methyl bromide (prepared from sodium bromide, sulfuric acid, methanol, and water) in DMF in a closed swing-top beer bottle. When the reaction was finished, the DMF solution along with precipitated KBr was added to several times their volume of water and the product (2,5-dimethoxybenzaldehyde) filtered and washed with cold water. This benzaldehyde may also be prepared through bromination of 1,4-dimethoxy benzene (dimethylation of hydroquinone with methyl bromide), formation of the Grignard reagent with magnesium in THF or ether, and reaction with DMF. 2,5-dimethoxybenzaldehyde was condensed with nitromethane through ammonium acetate catalysis using Shulgin’s method (PiHKAL) without removal of excess nitromethane, and recrystallized from isopropanol.
Reduction: While reduction of the nitrostyrene may be carried out using the well-known aluminum-mercury amalgam (see the Rhodium archive), the following is convenient if sodium borohydride is available. 10 mL ethanol, 18 mL ethyl acetate were combined in a 50 mL beaker with a magnetic stir bar, with a room temperature water bath. 1.00 g NaBH4 was added and allowed to stir for 1 minute, then 0.79 g 2,5-dimethoxynitrostyrene was added portion-wise, allowing the yellow/orange color to disappear before each addition. The temperature of the reaction remained between 23° C and 28° C. Stirred at 26° C for 30 minutes after final addition. 20 mL dH2O and some 99% acetic acid were added to neutralize NaBH4, and the phases separated. The aqueous phase was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and distilled, using aspirator vacuum to remove last traces of solvent. This yielded 0.80 g of a dark yellow oil, consisting mostly of 2,5-dimethoxynitroethane.
0.87 g nickel chloride hexahydrate was dissolved in 36 mL methanol and this solution was added to the 0.80 g of residue from the above experiment, which quickly dissolved. The solution was cooled to 2° C with an ice bath and 0.70 g NaBH4 was added portion-wise. The temperature rose to 12° C. Stirred in ice bath for 1 hour. 15 mL dH2O were added, and the solution made acidic with 4 mL 2 N HCl, then ~0.8 mL conc. HCl. Stirred for a few minutes, then filtered into a separatory funnel, washing with 50 mL dH2O plus a few squirts from a wash bottle. Washed with 50 mL ethyl acetate, basified to pH 11.5 with 25% KOH (NaOH works fine, but was not on hand). Extracted with 40 mL then 2 X 20 mL ethyl acetate, filtered extract to break emulsion and remove nickel hydroxide. Organic extractions were washed with 10 mL dH2O, adding salt to break the emulsion, then washed with 30 mL brine. Dried over MgSO4. Solvent was distilled, leaving 0.36 g of amber-colored oily residue (mostly 2,5-dimethoxyphenethylamine base, ~55% yield).
Iodination: The following iodination is much simpler, safer, and available then that given by Shulgin, and provides a fairly clean product. The residue from above was dissolved in 40 mL ethanol in a 100 ml round-bottom flask. 1.02 g iodine was added with stirring, followed by 1.25 g Ag2SO4 (prepared by adding PPB sulfuric acid to a solution of silver nitrate, filtering and washing with water). Stirred at room temperature for 19 hours, filtered to remove yellow solids. This gave a light brown solution with the same appearance as before iodine was added. The solvent was distilled to yield 1.53 g tan residue.
To this residue was added 60 mL 5% NaOH and 30 mL dichloromethane (DCM). Stirred 5 minutes, separated, extracted with 3 X 20 mL DCM. The organics were pooled, washed with 50 mL dH2O then extracted with 4 X 20 mL 0.1 N HCl. Basified to pH 13 with 25% KOH and extracted with 5 X 20 mL DCM. Washed with 30 mL dH2O, filtered through solid NaCl, and dried over MgSO4. The solvent was distilled and 10 mL conc. HCl were added to the residue. Cooled, filtered, and air-dried to yield 0.14 g tan-white powder with a melting point of 250° C (2C-I hydrochloride).
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