CH3O    /\\     / \     NH2
    \ /    \\ /     \ /
     ||      |
     ||      |
     ||      |       ^
    / \    // \      |
  Br    \//    OCH3  +------------ the first (alpha - carbon)

Doses are 12-24mg, Duration is 4-8 hours.  Doses of 100mg have been taken
safely.  2C-B seems to be an extraordinarily colorful hallucingen similar
to LSD -- apparently somewhat analytical and dissasociative in higher doses
or in those sensitive to those effects.
Quote from Ecstasy: The MDMA Story...
[begins with a quotation from Alexander Shulgin]:
      2C-B... is a tool...  which ties the mental processes directly
    and constructively into the physical soma.
      The analgesic effects experienced with many, if not most,
    psychedelic drugs, are not present with 2C-B.  On the
    contrary, there is increased body awareness of every kind,
    including skin sensitivity, heightened responsiveness to
    smells, tastes, and sexual stimulation.
      One experiences increased consciousness of physical
    health and energy, or, on the other hand, sharpened
    awareness of any body imbalance or discomfort.
      2C-B allows for rich visual imagery and intesnse eyes-
    closed fantasy without the cluttering up of the mental field
    with too much elaboration...  It is a superb tool for learning
    and growth.
[...] At high doses (above 30 mgs.), 2C-B is intensely hallucinogenic,
and, like any major psychedelic, can be frightening for certain people.
In small doses, it becomes a mild sensory enhancer but does not have the
strongly empathogenic qualities that MDMA has.
    Perhaps the best use that has been found for 2C-B is as a synergist
with MDMA.  When taken together, the MDMA pushes the non-specific 2C-B
reaction in a more warm and emphathetic direction.  Because 2C-B is a
psychedelic drug, and therefore not fully predictable, its action can take
the user in many different directions.  But if the set and setting are right,
2C-B can enhance the desire for sexual orgasm during an MDMA experience.
The synergy of the two substances can on occasion be a true aphrodisiac.
Shulgin writes in PiHKAL:
"The most succesfful reports have followed a program in which the two drugs
are not used at the same time, nor even too closely spaced.  It appears that
the optimum time for the 2C-B is at, or just before, the final baseline
recovery of the MDMA."
DOB:  2,5-Dimethoxy-4-Bromoamphetamine.  The only chemical difference is
      the addition of an extra carbon to the chain.  This turns the
      phenethylamine into an alpha-methyl-phenethylamine (because the
      addition of a carbon means attatching a methyl group to the
      alpha carbon of the phenethylamine) also called a phenylisopropylamine
      or simply an amphetamine.

CH3O    /\\     / \     NH2
    \ /    \\ /     \ /
     ||      |       |
     ||      |       |
     ||      |       CH3
    / \    // \
  Br    \//    OCH3
 
DOB has a potency of 1.0-3.0 mg and duration of 18-30 hours.  Its very
similar to LSD.  It seems to be more colorful than LSD and less dissociative
than 2C-B based on the reports I've read.  The index of safety is probably
something like over 1,000 times the effective dose.
2C-D (LE-25): 2,5-Dimethoxy-4-Methylphenethylamine.  This is the 2 carbon
     homologue of DOM (2C-B is to DOB as 2C-D is to DOM).  The difference
     between 2C-D and 2C-B is simply the replacement of the Br atom with
     a methyl group.
CH3O    /\\     / \     NH2
    \ /    \\ /     \ /
     ||      |
     ||      |
     ||      |
    / \    // \
 H3C    \//    OCH3
2C-D has a potency of 20-60mg and a duration of 4-6 hours.  Seems to also
be very colorful.  Shulgin notes:  "Wow! This particular compound is what
I call a pharmacological tofu.  It doesn't seem to do much by itself, always
teasing, until you get to heroic levels.  But a goodly number of experimental
therapists have said that it is excellent in extending the action of some
other materials.  It seems to boost the waning action of another drug, without
adding its own color to the experience."  At 150mg+ it appears it might be
a full blown 2C-B-like psychedelic, however.  No info on the toxic dose.
DOM (STP): 2,5-Dimethoxy-4-Methylamphetamine.  Again, simply the addition
    of an extra carbon to the chain to turn the phenethylamine 2C-D into
    the ampehtamine DOM.  And the replacement of the Br atom in DOB with
    a methyl group would give you DOM also.
 
CH3O    /\\     / \     NH2
    \ /    \\ /     \ /
     ||      |       |
     ||      |       |
     ||      |       CH3
    / \    // \
 H3C    \//    OCH3
DOM has a potency of about 3-10mg and a duration of 14-20 hours.  This was
first synthesized by Shulgin, and is what he calls his "Problem Child" (in
reference to Albert Hofmann's name for LSD).  It gained a considerable
amount of use in the 60's and people taking 30mg+ (a whopping dose) had
some very dissasociative, bad trips.  It was known as STP, which stands for
the motor oil additive actually, but was also known as "Serenity,
Tranquility and Peace".  From the descriptions it seems LSD-like, with
possibly even more of a head-trip.  5-10mg seems *much* more appropriate
from the descriptions with very good effects.  Only at higher (20-30mg)
doses does it appear to get really nasty.
And for chemical comparison, MDA and MDMA:  3,4-methylenedioxyamphetamine and
3,4-methylenedioxymethamphetamine respectively...  They're somewhat similar
to DOM and DOB -- all the ring substituents need to be knocked off and
replaced with the 3,4-methylenedioxy ring.  Then for MDMA you've got the
addition of a methyl group to the nitrogen amine.
MDA:
     O     /\\     / \     NH2
   /   \ /    \\ /     \ /
  /     ||      |       |
H2C     ||      |       |
  \     ||      |       CH3
   \   / \    //
     O     \//
MDMA:
 
     O     /\\     / \     NHCH3
   /   \ /    \\ /     \ /
  /     ||      |       |
H2C     ||      |       |
  \     ||      |       CH3
   \   / \    //
     O     \//
Also we might as well throw in amphetamine if you all haven't figured out
what that should look like yet (replace the NH2 with NHCH3 to get
methamphetamine -- identical substitution as between MDA and MDMA).
Also, if you knock off the CH2 from amphetamine, you'll get phenethylamine
which is the prototype chemical for all the drugs I've listed so far, although
itself its inactive.
amphetamine:
    /\\     / \     NH2
  /    \\ /     \ /
 ||      |       |
 ||      |       |
 ||      |       CH3
  \    //
    \//
 
And just for kicks here we have good old LSD which looks nothing like all
these other chemicals:
                     / C2H5
          H.     CON
            '. /     \ C2H5
             / \
           /     \
          ||      |
          ||      N
   /\\    /\     / \
 /   \\ /    \ /     CH3
||     |      | \
||     |      |   H
 \   // \    /
   \//    \/
    |     ||
    |     ||
   HN-------
Hope you enjoyed that.  Chem dweebs please check to make sure I got
everything correct.  I didn't have time to go over this with a fine-toothed
comb.
=============================================================================
From: cutrell@nic.cerf.net (Doug Cutrell)
Date: 8 Jul 92 23:31:16 GMT
Newsgroups: alt.drugs
Subject: Re: LSD.
Lamont Granquist writes:
>DOB has a potency of 1.0-3.0 mg and duration of 18-30 hours.  Its very
>similar to LSD.  It seems to be more colorful than LSD and less dissociative
>than 2C-B based on the reports I've read.  The index of safety is probably
>something like over 1,000 times the effective dose.
This figure is probably based on animal experiments described
by Shulgin in Pihkal.  However, he goes on to say that the
index of safety is probably much lower than this.  He says
there are numerous reports of overdoses causing vascular
arterial spasm, and gives one verified account of a couple who
thought they had MDA and took quantities appropriate for that
compound... i.e. around 100 mg.  The woman died, the man lived
after convulsions and a week in a coma.  Since the standard dose
is 1-3 mg., the lethal dose is more like 30 times the effective
dose.
Doug Cutrell
cutrell@cerf.net
=============================================================================
        Well, in a thread recently, there was some talk aabout bromo
mescaline, and mention was made of the entry in the Student Handbook of
our esteemed institution that deals with the drug in question.  Well, it is
Reed folklore that tells us that bromo mescaline was first synthesized here
at Reed (BTW, it is not folklore that Dr. Demento graduated from Reed),
but the drug is real, to which several friends can attest.  Since I have the
ol' Student Handbook right in front of me, I'll tell y'all what it sez.
----------------------------------------------------------------------------
From _The Reed College Student Handbook_, in the "Drug Article That Ate Reed
College", by Marty Smith:
   Bromo-mescaline. The most terrifying hallucinogen known to man. The effects
last 3-5 hours, the visuals are awe-inspiring and the head trip is light,
usually.  The catch is, first, for it to act like bromo, you have to snort
it. This is really intense, because in about two to five minutes, you're
tripping you ass off, the world is melting. The incredible speed with which
this happens is one of the things those who like it like about it. However,
when it gets up your nose it hurts. This is probably an understatement. It's
really amazingly painful. You'll be suprised that you would actually do this
to yourself. It has been described as having red hot knives shoved up your
nose, or being kicked in the face by a psychedelic horse. You may briefly
entertain notions of dying.  This all dies down after about twenty minutes,
though, and you're lucky there will be no nausea at all afterward. (It helps
to have eaten a starchy meal about an hour and a half earlier.) Otherwise,
you might have about 20 minutes of mild nausea. The visuals are real good.
To have visuals this intense on acid you'd have to be on so much that you
couldn't talk.  On bromo you could discuss them reasonably coherently.
   A word about dosage. One hit is one fourtieth of a gram.  This is a
fact. Do not say something stupid like, "Oh, let's do a lot," and hoot up a
couple of lines the size of your thumb. I have some friends who did this,
and they ended up lying under some bushes, at night, in the rain, unable
even to yell for help, and now they will not do drugs for the next five
million jillion years.
---------------------------------------------------------------------------
That's the straight dope (none of the many puns intended).
late,
miguel
=============================================================================
pierre@media.mit.edu (Pierre St. Hilaire) writes:
>       Sure. And table salt releases sodium and chlorine in your
>body, so you will both catch fire and suffocate if you take it.
>
>       Adding halogen atoms to psychedelic amines can significantly
>modify their potency, duration, and effects. Read Alexander Shulgin's
>PIKHAL for an extensive discussions on halogenated substituted
>phenylethylamines.
yes, i believe that "bromomescaline" 2-CB aka CBr...  2,5-dimethoxy-4-
bromophenethylamine.  the reason why it probably burns going up your nose
is that it may lack any kind of anaesthetic action (unlike MDA, MDMA, and
particularly cocaine), while still being in the form (probably) of a
hydrochloric salt (where the HCl comes from).
culled from the MDMA FAQ:
}
} CBr is 2,5-Dimethoxy-4-Bromophenethylamine.  The
} "sometimes frightening" part probably comes from taking more than the
} full dose, and the literature suggests that with larger dosages come
} disproportionately larger responses, unlike some other psychedelics
} we all know and love.  I've had very enlightening experiences with CBr,
} and they grew better in quantum leap fashion.
}
} +  wonderful and gently insightful (semi-wilderness, daytime, friends).
} +  profoundly sexual with glimpses of bird-animal forms (indoors, nightime,
}    lover) minor telepathic imagery.
} +  sexual and shamanic, native american imagery (indoors, day-night, alone).
} +  profound native american imagery (indoors, night, after cannabis, friend)
}    actually slept a bit (too much cannabis) and awoke to the most wonderful
}    visuals (friend in other room - ditto).
} +  full-blown spirit animals all night long (desert, night, friend, good THC
}    1/2 way thru trip) - mountain lion (very playful) and eagle most prominent
}    two deer (incredibly loving), a wolf (very brief), fantastic living plant
}    spirits, entities in mountain, mucho native american imagery, et. al.
}    very telepathic with friend.  brief teleportation/desert-zoom experience.
}    understood the ancients' fascination with constellations.  imparted with
}    sudden knowledge in extreme detail - confirmed later by ex-lover, scared
}    ex-lover shitless.
}
} My last experience with CBr changed my life in many profound ways (for the
} better).  With THC and a little concentration I can get back to some of those
} places.  With no THC and a lot of concentration I can get back to some of
} those places.  Remember.
}
} I believe CBr is recognized as an enthogen and an entactogen, and
} unfortunately it's now Schedule 1. :-(   Put this one on the top of
} the list of drugs to be legalized.
 
=============================================================================
Date: Sun, 28 Feb 1993 00:22:14 -0800
From: Alexander T. Shulgin
To: lamontg@milton.u.washington.edu
Subject: bromo
} Hi:
}
} There has been quite a flow of stuff on the subject of BROMO on
} alt.drugs entry.  Maybe you can post some parts of the following
} that might answer some of the comments, questions, or errors
} being put out there on the topic.
}
} (1)  Bromomescaline is without doubt 2C-B.  The dosage, the
} duration, the nature of the experience, all seem consistent with
} this assignment.  Also, as you have indicated, the replacement of
} a methoxy group (of mescaline) with a bromo atom gives the
} isomeric structure (a little rearrangement needed) of 2C-B.
}
} (2)  It releases bromic acid.  Of course not.  Bromic acid
} (HBrO3) is an unstable chimera which is substantially unknown.
} Probably what is meant is that it releases hydrobromic acid
} (HBr) but then there is no experimental evidence that HBr is
} released either.  I suspect that the bromine atom stays on the
} drug molecule all the way through the kidney, and that there
} is no release of this element at any time in the body.
}
} (3)  It is illegal, or a scheduled drug.  No so.  2C-B was added
} to the German law in January of this year, but in the US it is
} still an unnamed drug in Federal law.
}
} (4)  It burns on snorting (insufflation).  It sure does, but this
} is most likely due to the fact that it is extremely insoluble in
} water, and probably sits on the mucous membranes for quite a
} while until it dissolves and is absorbed.  And until this happens
} it irritates and blisters the skin at the sites where the solid
} particles of the drug happen to settle.  Once absorbed, the
} pain disappears, and the effects start.  A challenge to this
} would be to snort the acetate or the hydrobromide salt, both of
} which are quite a bit more soluble in water.  These should have
} the same psychological effect, and they should act even more
} quickly (no slow dissolving) and act with little or no pain.
}
} I would love to know who in the wide wide world of information
} input discovered the term bromic!!  It cannot believe it has any
} merit.
}
} Can you drift some of this on to the world of alt.drugs and
} satisfy this search for information?
}
} Thanks.
}
} Sasha
=============================================================================
From: Mark_Farone@sfa.ufl.edu (Mark Farone)
Newsgroups: alt.psychoactives
Subject: Re: 2CB
Date: 18 Apr 1994 12:28:10 GMT
Message-ID: <Mark_Farone-180494082742@128.227.37.18>
In article <766538637-0-4072@chop.isca.uiowa.edu>, David Roknich
<Hologram@chop.isca.uiowa.edu> wrote:
> dg596@cleveland.Freenet.Edu (Russell Faraday)writes:
> Another new sensation gripping our little pocket of cultural
> coolness is something called 2CB.  As a discussion starter, I'd
> ......
> 2CB is a designer drug that was not illegal until a few morons
> blathered publicly about its existance in the early 80s
With respect to US laws, 2cb (aka Nexus, Zenith) wasn't scheduled until
late 1993.
Its actual chemical name is 4-Bromo-2,5-Dimethoxyphenethylamine.
The Feds were alerted when a rather rich fella in Tampa, FL took some to
relieve impotence, as it was being promoted. When started tripping he
called the DEA and the next thing you know...
See _Federal Register_, Vol. 58, No. 212, Thurs. Nov 4,1993 page 58819-20.
--
__________________________________________________________________________
Mark Farone               "A pile of rocks ceases to be a rock pile when
University of Florida         somebody comtemplates it with the idea
Mark_Farone@sfa.ufl.edu          of a cathedral in mind." -Saint Exupery
=============================================================================
From: bgg@connect.com.au (Ben Golding)
Newsgroups: alt.drugs
Subject: 2CB report from Sydney Morning Herald (18 May 94)
Date: 20 May 1994 11:34:39 +1000
Message-ID: <2rh43f$81k@warrane.connect.com.au>
A wonderfully fact-free article from the SMH.
Operation Noah is an annual campaign where people are encouraged to
call the police to dob in a drug users and suppliers.  Over the years
it has been running it has been steadily galvanising public opinion
against the operation and pushing discussion of drug policy to the
fore.  As you can imagine, most of the busts are people with a plant
in their backyard with neighbours who don't like them, you know,
exactly the sort of people that pose the greatest threat to society.
        Ben.
--
Noah Hunts New Drug, Emma Tom, Sydney Morning Herald, Wed.18th, 1994
        A dangerous new designer drug similar to ecstasy is among the
amphetamines to be targeted today in operation Noah, the annual national
drugs phone-in.
        Detective Sergeant Mal Brammer, from the NSW Drug Enforcement
Agency, said the new drug, known as nexus or 2CD (sic), had originated
at dance parties in the United States.
        He said nexus differed from ecstasy in that it was stronger,
lasted longer and caused hallucinations. Part of its attraction was that
it "temporarily alleviated impotency and frigidity".
        "We are concerned that nexus is being mixed with or sold as
ecstasy," he said.
=============================================================================
From: bgg@connect.com.au (Ben Golding)
Newsgroups: alt.drugs
Subject: Re: 2CB report from Sydney Morning Herald (18 May 94)
Date: 21 May 1994 12:56:56 +1000
Message-ID: <2rjt9o$ip6@warrane.connect.com.au>
[quoted text deleted -cak]
Further to this article, Here's a response to the letters page:
Re: "Noah hunts new drug",  Emma Tom, April 18th 1994, p.10
Before we panic about a new designer amphetamine, which Nexus is not, I
feel some clarification is in order.  I am a medicinal chemist in
regular contact with Dr. Alexander Shulgin, who has devoted his life to
producing new drugs for use in therapy, and names 2C-B (not 2CD) as his
greatest discovery.  Not originating at dance parties, it has been
known to the scientific community for years.  Concerning legality: the
NSW poisons list prohibits chemicals of its class with hallucinogenic
properties.  2C-B is unlisted, and its hallucinogenic properties
debatable .  It does not cause true hallucinations but visual
distortions at high do ses, and is subjectively different from other
drugs such as ecstasy.  It is not a stimulant, and lacks side-effects
such as overheating and post-use fatigue.  Unlike LSD it leaves the
user mentally clear and lucid, and so is unlikely to cause a panic
reaction.  As for dangerous, 2C-B is essentially non-addictive, rel
atively short acting, has no known serious side-effects, and no
recorded overdose cases.  Legal or illegal, like it or not, it will
probably be increasingly popular.
=============================================================================
Newsgroups: alt.drugs
From: bprofane@netcom.com (Gert Niewahr)
Subject: Re: long term effects of 2cb?
Message-ID: <bprofaneCDDz5x.yJ@netcom.com>
Date: Wed, 15 Sep 1993 08:20:20 GMT
In article <2735jl$kcj@agate.berkeley.edu> bbehlen@soda.berkeley.edu (Brian Behlendorf) writes:
>       After peusing the various net.resources on the subject, as
>well as checking PiHKAL, I haven't been able to find any info on
>possible long-term effects of 2CB.  Anyone have any recent info
>on this?  I suppose I could ask Shulgin, since he's teaching a
>class here at Cal....
If you mean 2C-B toxicity tests equivalent to those done for MDMA
(Ecstacy), no, I haven't heard of any.  Those neurotransmitter
degradation tests filtered out to the net pretty quickly too, so I'd be
half surprised if a 2C-B evaluation was underway that we haven't heard
about.
I'd offer the same lay demographic survey I described at length a few
years ago to rebut the MDMA toxicity tests: As an undergraduate, I was
part of what was effectively a test group of 18-21 year-old college
students regularly consuming very pure phenethylamines (mainly MDMA and
2C-B).  This group was large enough to be statistically stable (500+
subjects) yet so homongenous in terms of intelligence, motivation,
education, and background as to form a narrow behavioral profile.
Moreover, this group was complemented by an otherwise identical control
group of about 700 subjects.  Both groups can be characterized as highly
intelligent (having had to score in the top 5th percentile of most
standardized tests in order to be part of either group) and destined for
careers demanding high intellectual ability.
As I noted a few years back, the differentiation between these two groups is
effectively zilch.  The most significant statistic characterizing samples
of this type of subject (i.e., graduates of this college) is that about
one in five attains a PhD, the highest percentage for non-science
universities in the US.  Almost half finish some kind of graduate
degree.  It's a little early, even after ten years, to evaluate whether
these groups have or will attain the norms, but it looks like both are
on track.  In fact, the per capita numbers are climbing a little.
Unless the puritans are working overtime to make up for the druggies,
both parties are on the beam.
But, as I say, the differentiation is nil.  I knew a large percentage of
both groups personally, and as I look over the class notes, knowing who
did what, I see no sign that the two groups are diverging in terms of
the gross career achievement profile.  Lots of lawyers and MDs on both
sides of the fence.  Lots of papers being published by grads of both
stripes.  In fact, some of the most notorious drug chemists (who cooked
up most of the X and bromo we all ingested) are post-docs or teaching
faculty already.  (Yes, that bright young assistant prof. teaching
organic may have been whipping up job lots of X not that long ago.)
Yes, this is a very rough demographic analysis.  I can't hand out
questionaires about past drug use and current grad school at reunions.
But I'm also close enough to feel empirically confident about the
profiles, and I've seen serious studies published that relied on smaller
and more dubious samples that this.
Oh, I should make it clear, in light of Brian's question, that about
35-40% of the phenethylamines ingested were 2C-B, by my estimation.
That's a lot, given the per capita volume.  It was quite easy to score
5-10 grams a pop.

                                             http://www.TpB.org