pill_jockey
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If you are going to dissolve it in water make sure you use distilled water not normal tap water, as the chlorine will destroy the LSD which wouldn't make you a very happy tripper
LSD and Tap Water
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phase_dancer
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^^ Absolutely. Thanks for that pill_jockey
Psychadelic_Paisly
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P_D, if you had the time and patience, would you be able to throw in some graphics and explanations of how the chlorine interacts with the bonds of LSD.
I am (and hopefully others) intrigued to understand this. I have a pretty good grasp of organic chem. (not to tech. though
)
Thanks.
I am (and hopefully others) intrigued to understand this. I have a pretty good grasp of organic chem. (not to tech. though
)Thanks.
phase_dancer
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LSD and Chlorine; Mechanisms of nucleophilic addition
Psychadelic_Paisly, I realise you probably understand much of this already, but to hopefully broaden the general reader understanding, I’ve started with some pretty basic stuff. Although it might not initially seem like a difficult task, it has proved to be quite daunting, as to grasp it properly, it is necessary to have an understanding of nucleophilic addition chemistry, and more importantly, the effect of substitutions on rates of addition. All pretty deep stuff. So I’ll take it as far as I dare. Maybe Biscuit can fill in the gaps, and better still, pull me up on anything incorrectly or badly explained. Smileyfish may like to correct or expand on Chlorine in tap water.
Here goes….
Chlorine in Tap Water
Chlorine is a particularly reactive element, often more reactive than the other halogens including fluorine (try sticking a fluoride ion on a benzene ring). The reactivity of the many Chlorine reactive species’ is why most harmful bacteria present in our drinking water catchments, reservoirs and dams, are killed before the water reaches us. Chlorine in tap water is also the reason some 5,000 or more Americans die from cancer every year, although many more would die without it. As it very soluble, chlorine gas is usually bubbled through water. Free chlorine can also be achieved by adding hypochlorite/ate salts.
Whether chlorination is the principle means of water purification, or is employed as a support for ozone treatment (as with our local tap water), the idea is to add (slightly) more chlorine than is considered necessary. Another means of chlorination uses monochloroamines, and while these may be less reactive towards LSD [questionable], some chlorine will be produced via enzymatic breakdown resulting in similar reactions as shown below.
One would then perhaps expect chlorine in tap water to be predominately made up of dissolved chlorine gas as Cl2, and Cl- ( chloride ions). There will however, also be some free radical chlorine (Cl*). In reacting with organic materials in the presence of other dissolved species, free radicals will produce other reactive species, too numerous to list. In the presence of LSD or a similar molecule of relative fragility, any of the resulting reactions with free radicals would effectively destroy the molecule.
Nucleophilic Addition & Free Radicals
When learning double bond addition chemistry, it is usual to describe the actions of halogens on the ethylene molecule ( CH2=CH2 ). Different mechanisms exist for nucleophilic attack when chlorine ( & Bromine & sometimes Iodine) exists either as a gas (Cl2), as the chloride ion (Cl-) (present as hydrochloric acid H+Cl-), and as a free radical (Cl*). If addition across a double bond results in a mono-halo-compound, Markivnokov orientation usually occurs which says the halogen will bond to the most substituted carbon. Radical addition however, is non-Markivnokov, resulting in the halogen attaching to the least substituted carbon. Relating this to the susceptible double bond of LSD, position 9 is the least substituted of the two.
Free radicals are often produced by the action of UV (sunlight) on water containing dissolved chlorine, but small amounts are produced with seemingly no such energy source. To prevent Cl* forming in the lab, special reaction conditions are usually employed. During the formation of Cl- free ions in tap water purification, some free radicals would also be produced. These may destroy several molecules before forming more stable Chloro-LSD compounds. Other parts of the LSD molecule are also susceptible to attack by free radicals.
Susceptibility of LSD's weak double bond to nucleophilic attack
The double bond on the LSD molecule (across positions 9 & 10) differs somewhat from the ethylene molecule. This has to do with electron densities, conjugation, and other effects from bonded and neighboring groups (an in-depth look perhaps being a bit beyond the scope of this explanation /hypothesis).
This double bond (across positions 9 & 10) is very fragile because of differences in electron density across the pi bonds, due among other things to the effects of substituted groups on each carbon (9 & 10).
When exposed to tap water, the relative concentrations of each substance present (Chlorine and LSD) ultimately equates to using a molar excess of Chlorine in the lab.
Molecular weights and the destructive relationship of chlorine and LSD
The amounts of Chlorine present in tap water should be no more than 5mg/L. 10 mL therefore contains a possible 0.05mg or 50ug of Cl2 (or Cl-) At first glance it doesn't seem that much, with reason saying a large drop (~ 100uL) of water contains a miniscule 0.5ug
To get an initial idea of how much this actually represents, we look at what reacts with what. We are not concerned with direct weight for weight relationships, but rather in the molar relationship of the substances. If an ideal chemical reaction states:
Compound A + Compound B = Compound C
To a chemist, this implies 1 mole of A reacts with one mole of B to produce 1 mole of C. It does not say 1 gram of A + 1 gram of B = 1 gram of C. Atomic weights (found on most periodic tables) are added together for each element present, to give the molecular weight = to 1 mole of a compound.
Example 1: 1 mole of pure water equals approximately 18 grams
H = 1.0079g
O = 15.999g
therefore H2O = ~18, which means 1 mole of water is ~18g.
Of course it’s possible to have far less than 1 mole of a substance, but if conditions exist so that substance A reacts mole for mole with substance B, it only takes a corresponding amount of the substance B (in moles) to potentially alter all of the substance A.
Example 2: How 50ug of Chlorine "equals" 235ug of LSD
1 mole of Chlorine (Cl2) = ~70.9g (also = to 2 x 35.45g of Cl-)
1 mole of LSD = 323.44g,
50ug of Chlorine = 0.00005g / 70.90g = 7.05 E-07 moles
50ug of LSD = 0.00005g/ 323.44g = 1.50E-07 moles
Therefore, on a molar basis, if 1 mole of chlorine reacts with 1 mole of LSD, expressing that as a weight for weight value means 1 gram of chlorine would destroy 4.7 grams of LSD (from above; 7.05 / 1.5 = 4.7)
Referring to Reactions in 1,2,3 and 4 listed below
In this way, 1 mole of LSD can react with 1 mole of chlorine as Cl2. But as reaction 3 demonstrates, in the presence of water the reaction goes further, releasing 1 chlorine ion, which may in turn react with another LSD molecule via reaction 2
In the above reasoning, it is assumed 1 mole of chlorine will react with 1 mole of LSD. This means 50ug of Cl2 can destroy 235ug of LSD. But if a chloride ion was to be generated each time, this could effectively mean 470ug of LSD may be destroyed by 50ug of Chlorine. Unfortunately, it does not stop there. This is merely one reaction sequence which may occur, and it is less severe by far than the free radical mechanism of Reaction 4 (below).
Example 3; Typical reactions involving LSD and Chlorine
Representative of many similar reactions, any of the following 4 examples will result in the de-activation of LSD’s psychotropic properties.
Reaction:
These steps in Reaction 4 should be looked upon as likely first steps rather than a beginning to end fate of LSD in the presence of a Chlorine radical. Other rearrangements, intra and intermolecular reactions would also occur over time, possibly producing structures only remotely similar to that of the original LSD molecule.
Diagram 1: Proposed mechanisms involved in Reaction 3:
Adapted from "Mechanism in Organic Chemistry" by Peter Sykes & "Organic Chemistry" by John McMurry
Psychadelic_Paisly, I realise you probably understand much of this already, but to hopefully broaden the general reader understanding, I’ve started with some pretty basic stuff. Although it might not initially seem like a difficult task, it has proved to be quite daunting, as to grasp it properly, it is necessary to have an understanding of nucleophilic addition chemistry, and more importantly, the effect of substitutions on rates of addition. All pretty deep stuff. So I’ll take it as far as I dare. Maybe Biscuit can fill in the gaps, and better still, pull me up on anything incorrectly or badly explained. Smileyfish may like to correct or expand on Chlorine in tap water.
Here goes….
Chlorine in Tap Water
Chlorine is a particularly reactive element, often more reactive than the other halogens including fluorine (try sticking a fluoride ion on a benzene ring). The reactivity of the many Chlorine reactive species’ is why most harmful bacteria present in our drinking water catchments, reservoirs and dams, are killed before the water reaches us. Chlorine in tap water is also the reason some 5,000 or more Americans die from cancer every year, although many more would die without it. As it very soluble, chlorine gas is usually bubbled through water. Free chlorine can also be achieved by adding hypochlorite/ate salts.
Whether chlorination is the principle means of water purification, or is employed as a support for ozone treatment (as with our local tap water), the idea is to add (slightly) more chlorine than is considered necessary. Another means of chlorination uses monochloroamines, and while these may be less reactive towards LSD [questionable], some chlorine will be produced via enzymatic breakdown resulting in similar reactions as shown below.
One would then perhaps expect chlorine in tap water to be predominately made up of dissolved chlorine gas as Cl2, and Cl- ( chloride ions). There will however, also be some free radical chlorine (Cl*). In reacting with organic materials in the presence of other dissolved species, free radicals will produce other reactive species, too numerous to list. In the presence of LSD or a similar molecule of relative fragility, any of the resulting reactions with free radicals would effectively destroy the molecule.
Nucleophilic Addition & Free Radicals
When learning double bond addition chemistry, it is usual to describe the actions of halogens on the ethylene molecule ( CH2=CH2 ). Different mechanisms exist for nucleophilic attack when chlorine ( & Bromine & sometimes Iodine) exists either as a gas (Cl2), as the chloride ion (Cl-) (present as hydrochloric acid H+Cl-), and as a free radical (Cl*). If addition across a double bond results in a mono-halo-compound, Markivnokov orientation usually occurs which says the halogen will bond to the most substituted carbon. Radical addition however, is non-Markivnokov, resulting in the halogen attaching to the least substituted carbon. Relating this to the susceptible double bond of LSD, position 9 is the least substituted of the two.
Free radicals are often produced by the action of UV (sunlight) on water containing dissolved chlorine, but small amounts are produced with seemingly no such energy source. To prevent Cl* forming in the lab, special reaction conditions are usually employed. During the formation of Cl- free ions in tap water purification, some free radicals would also be produced. These may destroy several molecules before forming more stable Chloro-LSD compounds. Other parts of the LSD molecule are also susceptible to attack by free radicals.
Susceptibility of LSD's weak double bond to nucleophilic attack
The double bond on the LSD molecule (across positions 9 & 10) differs somewhat from the ethylene molecule. This has to do with electron densities, conjugation, and other effects from bonded and neighboring groups (an in-depth look perhaps being a bit beyond the scope of this explanation /hypothesis).
This double bond (across positions 9 & 10) is very fragile because of differences in electron density across the pi bonds, due among other things to the effects of substituted groups on each carbon (9 & 10).
When exposed to tap water, the relative concentrations of each substance present (Chlorine and LSD) ultimately equates to using a molar excess of Chlorine in the lab.
Molecular weights and the destructive relationship of chlorine and LSD
The amounts of Chlorine present in tap water should be no more than 5mg/L. 10 mL therefore contains a possible 0.05mg or 50ug of Cl2 (or Cl-) At first glance it doesn't seem that much, with reason saying a large drop (~ 100uL) of water contains a miniscule 0.5ug
To get an initial idea of how much this actually represents, we look at what reacts with what. We are not concerned with direct weight for weight relationships, but rather in the molar relationship of the substances. If an ideal chemical reaction states:
Compound A + Compound B = Compound C
To a chemist, this implies 1 mole of A reacts with one mole of B to produce 1 mole of C. It does not say 1 gram of A + 1 gram of B = 1 gram of C. Atomic weights (found on most periodic tables) are added together for each element present, to give the molecular weight = to 1 mole of a compound.
Example 1: 1 mole of pure water equals approximately 18 grams
H = 1.0079g
O = 15.999g
therefore H2O = ~18, which means 1 mole of water is ~18g.
Of course it’s possible to have far less than 1 mole of a substance, but if conditions exist so that substance A reacts mole for mole with substance B, it only takes a corresponding amount of the substance B (in moles) to potentially alter all of the substance A.
Example 2: How 50ug of Chlorine "equals" 235ug of LSD
1 mole of Chlorine (Cl2) = ~70.9g (also = to 2 x 35.45g of Cl-)
1 mole of LSD = 323.44g,
50ug of Chlorine = 0.00005g / 70.90g = 7.05 E-07 moles
50ug of LSD = 0.00005g/ 323.44g = 1.50E-07 moles
Therefore, on a molar basis, if 1 mole of chlorine reacts with 1 mole of LSD, expressing that as a weight for weight value means 1 gram of chlorine would destroy 4.7 grams of LSD (from above; 7.05 / 1.5 = 4.7)
Referring to Reactions in 1,2,3 and 4 listed below
In this way, 1 mole of LSD can react with 1 mole of chlorine as Cl2. But as reaction 3 demonstrates, in the presence of water the reaction goes further, releasing 1 chlorine ion, which may in turn react with another LSD molecule via reaction 2
In the above reasoning, it is assumed 1 mole of chlorine will react with 1 mole of LSD. This means 50ug of Cl2 can destroy 235ug of LSD. But if a chloride ion was to be generated each time, this could effectively mean 470ug of LSD may be destroyed by 50ug of Chlorine. Unfortunately, it does not stop there. This is merely one reaction sequence which may occur, and it is less severe by far than the free radical mechanism of Reaction 4 (below).
Example 3; Typical reactions involving LSD and Chlorine
Representative of many similar reactions, any of the following 4 examples will result in the de-activation of LSD’s psychotropic properties.
Reaction:
- LSD + Cl2 = dichloro-LSD
- LSD + Cl- = chloro-LSD
- LSD + Cl2 + H2O = halohydrin-LSD + H+Cl- (see diagram 1 below)
- LSD + Cl* = Chloro-LSD* + HCl => Cl2 + Chloro-LSD* =Cl* + Chloro-LSD. Repeat over and over.
These steps in Reaction 4 should be looked upon as likely first steps rather than a beginning to end fate of LSD in the presence of a Chlorine radical. Other rearrangements, intra and intermolecular reactions would also occur over time, possibly producing structures only remotely similar to that of the original LSD molecule.
Diagram 1: Proposed mechanisms involved in Reaction 3:
Adapted from "Mechanism in Organic Chemistry" by Peter Sykes & "Organic Chemistry" by John McMurry
Last edited:
pill_jockey
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I take my hat off to you p_d once again a very informative yet easy to understand post.
I'm currently studying pharmcology at a Queensland university and have found alot of your previous posts to be very helpfully in my studies. Thanx
P.s I'm not sure if you want to but you might consider putting this in a seperate post in case someone is searching for information on how Chlorine reacts with LSD. They mihgt overlook this thread because of the name, i would hate for such a good post to go too waste
[Edit: Done, thanks for the tip pill_jockey; p_d]
I'm currently studying pharmcology at a Queensland university and have found alot of your previous posts to be very helpfully in my studies. Thanx
P.s I'm not sure if you want to but you might consider putting this in a seperate post in case someone is searching for information on how Chlorine reacts with LSD. They mihgt overlook this thread because of the name, i would hate for such a good post to go too waste
[Edit: Done, thanks for the tip pill_jockey; p_d]
Last edited by a moderator:
Psychadelic_Paisly
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Um........that was WAY more tech than my brain could contemplate.
But thanks P_D, while I did get lost it was still interesting and the more reading, the more you learn!
But thanks P_D, while I did get lost it was still interesting and the more reading, the more you learn!
phase_dancer
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Try reading it a few times. Let me know what is hardest to grasp, and I'll try to rephrase. It's mainly first year organic chem, but the the complexity of the molecule does extend this a wee bit. If there are any terms you find confusing, I'll expect you'll look them up But in all seriousness, I just forget sometimes, and when there's no chem illiterate person here to proof......so please mention if anyone thinks anything should be said more in laymans terms.
I don't really want to have to draw the radical mechanisms, but any good chem text should make it clearer. I really want to be able to convey this type of info, so don't hesitate to set a task or ask what may seem a difficult question. If I can't answer it I won't, but I'll try and search out an answer if I can.
I'll review it over the next day or so and touch up any hairy bits
[Just realised I haven't addressed the other notably fragile part of the molecule, the chiral carbon C8. Another day perhaps...
But in all seriousness, I just forget sometimes, and when there's no chem illiterate person here to proof......so please mention if anyone thinks anything should be said more in laymans terms.I don't really want to have to draw the radical mechanisms, but any good chem text should make it clearer. I really want to be able to convey this type of info, so don't hesitate to set a task or ask what may seem a difficult question. If I can't answer it I won't, but I'll try and search out an answer if I can.
I'll review it over the next day or so and touch up any hairy bits
[Just realised I haven't addressed the other notably fragile part of the molecule, the chiral carbon C8. Another day perhaps...
Last edited:
drinky_mcbeer
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hmm pd is smart ![:\](https://bluelight.org/xf/BL_Images/Orig_Emoji/wrygrin.gif "wry grin :\")
Urbanhog
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Speaking of water...... since LSD is supposed to be "hygroscopic" ???? or what?
So does the water tempetures play a important part? I mean would using room tempeture/warm distillered water affect the potency? so its best to use cool water? or the water traps all the LSD in the liquid?
If you "mixed" in water.... doesnt licking the glass dry make any differences if you are that tightarsed about "wastage", trying to get as much for your buck?
Cheers again phase for the very informative post.
Urbie
So does the water tempetures play a important part? I mean would using room tempeture/warm distillered water affect the potency? so its best to use cool water? or the water traps all the LSD in the liquid?
If you "mixed" in water.... doesnt licking the glass dry make any differences if you are that tightarsed about "wastage", trying to get as much for your buck?
Cheers again phase for the very informative post.
Urbie
aunty establishment
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Wow that's awesome, I had no idea! Thanks guys, you rule as usual (esp. p_d).
One (probably silly) question: if you didn't happen to have distilled water on hand for some reason (e.g. in the bush) could you use anything else, eg vodka?
One (probably silly) question: if you didn't happen to have distilled water on hand for some reason (e.g. in the bush) could you use anything else, eg vodka?
Psychadelic_Paisly
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Could you boil it and let it cool in an attempt to 'purify' the water?
phase_dancer
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^^ No, not good enough. Get distilled water. It's sold cheaply in bottles at your local supermarket.
If you use distilled water in your steam iron it will probably last much longer, and your laundry whites should also stay fabulously white and mark free
Remember to first clean your eyedropper ( and everything else used) in boiling (distilled) water. Oh, and don't use the kettle to boil it as it potentially contains lots of nasties.
Urbanhog said
Cool water is best. Always keep your acid cool (as in Kool-aid)
Just use a very small bottle. It's that simple. Don't use big glasses, tablespoons and other BIG things. If you can get them, use a sterile, disposable micropipette to acurately measure your doses. Might be able to get these at a pharmacy.
Think about it for a bit, and don;t rush in. Plan the procedure step by step. Get all your stuff ready well in advance, and don't even think about guessing. And remember, there's been lots of perfectly fine LSD destroyed during past dilution attempts.
Aunty wrote
People have been known to use alcohol, although I think I would use propanol or butanol if I ever needed to (and they were available). Ingredients in some liquor could also do considerable harm, but a good vodka is probably about as close as you'll get.
If you were out in the bush, you'd already be thinking ahead and arrange to catch the morning dew. No chlorine in that hopefully 8(
Remember to first clean your eyedropper ( and everything else used) in boiling (distilled) water. Oh, and don't use the kettle to boil it as it potentially contains lots of nasties.
Urbanhog said
Cool water is best. Always keep your acid cool (as in Kool-aid
) Just use a very small bottle. It's that simple. Don't use big glasses, tablespoons and other BIG things. If you can get them, use a sterile, disposable micropipette to acurately measure your doses. Might be able to get these at a pharmacy.
Think about it for a bit, and don;t rush in. Plan the procedure step by step. Get all your stuff ready well in advance, and don't even think about guessing. And remember, there's been lots of perfectly fine LSD destroyed during past dilution attempts.
Aunty wrote
People have been known to use alcohol, although I think I would use propanol or butanol if I ever needed to (and they were available). Ingredients in some liquor could also do considerable harm, but a good vodka is probably about as close as you'll get.
If you were out in the bush, you'd already be thinking ahead and arrange to catch the morning dew. No chlorine in that hopefully 8(
Last edited:
SupaDiscoBreaka
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Psychadelic_Paisly said:
No you can't.
You boil water if you want to disinfect it, not clean it of active and possibly destructive chems.
aunty establishment
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Thanks for the answer p_d, one more thing; is there any legitimate use for a micropipette?
randomblondeboy
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you'd be amazed how much 'questionable' paraphenalia i have aquired with no fuss when telling the retailer i'm "doing an art installation"